JP2012216818A - Charge transport material, organic electroluminescent element and light-emitting device, display unit or luminaire using that element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a charge transport material and an electroluminescent element which exhibit high efficiency and drive durability after high-temperature storage, and in which dark spot is unlikely to occur.SOLUTION: The charge transport material consists of a compound represented by the following formula (Xrepresents a sulfur atom or an oxygen atom. Rand Rrepresent, independently, an alkyl radical, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted with these groups. n101 represents an integer of 0-11, n102 represents an integer of 0-7, and a plurality of Rand Rmay be identical or different from each other. Lrepresents a single bond or a bivalent coupling group. Any one of R, Land Rincludes a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group, or a silicon atom coupling group).

Description

  The present invention relates to a charge transport material, an organic electroluminescent element, and a light emitting device, a display device, or a lighting device using the element.

  Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they emit light with high luminance when driven at a low voltage. An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do.

In recent years, the use of phosphorescent materials such as iridium (Ir) complexes and platinum (Pt) complexes has increased the efficiency of devices. In addition, a doped element using a light emitting layer in which a light emitting material is doped in a host material is widely used.
Development of the charge transport material contained in the host material used for a light emitting layer and other organic layers is also performed actively.
For example, Patent Document 1 discloses an organic electroluminescent device using a compound having a triphenylene structure, and describes an organic electroluminescent device using a compound in which dibenzothiophene and triphenylene are connected by a benzene ring. Patent Document 2 discloses an organic electroluminescent device using a compound in which dibenzofuran and triphenylene are connected by a naphthalene ring.

  On the other hand, in recent years, various display devices including an organic electroluminescent element have been widely used, and are required to operate stably for a long time under various environments. For example, in-vehicle applications such as in-vehicle applications require a long life (so-called durability), and the interior of the vehicle becomes quite hot during daytime driving or parking, so the characteristics are also maintained after high-temperature storage. There is also a need for no change. In addition, it is important that the organic electroluminescent element does not change its characteristics after being stored at such a high temperature from the viewpoint that it generates heat when driven to the same degree or more as a conventional light emitting device.

Special table 2010-535809 gazette International Publication WO2009 / 074087

  On the other hand, as a result of examining the characteristics of the organic electroluminescent device using the compounds described in Patent Document 1 and Patent Document 2, the inventors found that the efficiency and durability after high-temperature storage were insufficient. In addition, a new problem has been found that the occurrence of dark spots is confirmed.

  The problem to be solved by the present invention is to provide a charge transport material and an organic electroluminescence device that have high efficiency and high driving durability after high-temperature storage and are unlikely to cause dark spots.

  As a result of intensive studies by the present inventors, a compound containing a dibenzothiophene structure or dibenzofuran structure and a triphenylene structure has a specific substituent, so that efficiency and driving durability after high-temperature storage are high and dark spots are hardly generated. It has been found that charge transport materials and organic electroluminescent devices are provided.

  That is, the present invention can be achieved by the following means.

（一般式（１）において、Ｘ¹⁰¹は硫黄原子または酸素原子を表す。Ｒ¹⁰¹およびＲ¹⁰²はそれぞれ独立にアルキル基、アリール基、ヘテロアリール基、フッ素原子またはシリル基を表し、さらにこれらの基で置換されていてもよい。ｎ１０１は０〜１１の整数を表し、ｎ１０２は０〜７の整数を表し、複数のＲ¹⁰¹およびＲ¹⁰²は同一でも異なっていてもよい。Ｌ¹⁰¹は単結合または２価の連結基を表す。ただし、Ｒ¹⁰¹、Ｌ¹⁰¹およびＲ¹⁰²のいずれかは、フッ素原子、フルオロアルキル基、シクロアルキル基、シクロアルキレン基、シリル基、アルキルシリル基、アリールシリル基またはケイ素原子連結基を含む。）
［２］ 前記一般式（１）で表される化合物が、下記一般式（２）で表されることを特徴とする［１］に記載の電荷輸送材料。

（一般式（２）において、Ｘ¹¹¹は硫黄原子または酸素原子を表す。Ｒ¹¹¹、Ｒ¹¹²およびＲ¹¹³はそれぞれ独立にアルキル基、アリール基、ヘテロアリール基、フッ素原子またはシリル基を表し、さらにこれらの基で置換されていてもよい。ｎ１１１は０〜１１の整数を表し、ｎ１１２は０〜７の整数を表し、ｎ１１３は０〜４の整数を表し、複数のＲ¹¹¹、Ｒ¹¹²およびＲ¹¹³は同一でも異なっていてもよい。Ａ^A1〜Ａ^A5はそれぞれ独立にＣＨ（ＣＨの水素原子はＲ¹¹³で置換されていてもよい）または窒素原子を表し、ｍ１１１は０〜６の整数を表す。ただし、Ｒ¹¹¹、Ｒ¹¹²およびＲ¹¹³のいずれかは、フッ素原子、フルオロアルキル基、シクロアルキル基、シリル基、アルキルシリル基またはアリールシリル基を含み、ｎ１１１、ｎ１１２およびｎ１１３が同時に０になることはない。）
［３］ 前記一般式（２）におけるｍ１１１が１〜５であることを特徴とする［２］に記載の電荷輸送材料。
［４］ 前記一般式（１）で表される化合物が、下記一般式（３）で表されることを特徴とする［１］〜［３］のいずれか一項に記載の電荷輸送材。

（一般式（３）において、Ｘ¹²¹は硫黄原子または酸素原子を表す。Ｒ¹²¹、Ｒ¹²²およびＲ¹²³はそれぞれ独立にアルキル基、アリール基、ヘテロアリール基、フッ素原子またはシリル基を表し、さらにこれらの基で置換されていてもよい。ｎ１２１は０〜１１の整数を表し、ｎ１２２は０〜７の整数を表し、ｎ１２３は０〜４の整数を表し、複数のＲ¹²¹、Ｒ¹²²およびＲ¹²³は同一でも異なっていてもよい。ｍ１２１は０〜６の整数を表す。ただし、Ｒ¹²¹、Ｒ¹²²、Ｒ¹²³のいずれかは、フッ素原子、フルオロアルキル基、シクロアルキル基、シリル基、アルキルシリル基またはアリールシリル基を含み、ｎ１２１、ｎ１２２およびｎ１２３が同時に０になることはない。）
［５］ 前記一般式（１）におけるｎ１０１が０であることを特徴とする［１］〜［４］のいずれか一項に記載の電荷輸送材料。
［６］ 前記一般式（１）におけるｎ１０２が０〜２の整数である、［１］〜［５］のいずれか一項に記載の電荷輸送材料。
［７］ 前記一般式（１）で表される化合物が、ジベンゾチオフェン骨格およびジベンゾフラン骨格中の酸素原子および硫黄原子を除き、炭素原子および水素原子のみからなることを特徴とする［１］〜［６］のいずれか一項に記載の電荷輸送材料。
［８］ 前記一般式（１）で表される化合物が、シクロアルキル基を含むことを特徴とする［１］〜［７］のいずれか一項に記載の電荷輸送材料。
［９］ 一般式（１）で表される化合物の分子量が１２００以下である、［１］〜［８］のいずれか一項に記載の電荷輸送材料。
［１０］ 基板と、該基板上に配置され、陽極及び陰極を含む一対の電極と、該電極間に配置された有機層とを有し、前記有機層が、燐光発光材料と［１］〜［９］のいずれか一項に記載の電荷輸送材料を含有することを特徴とする有機電界発光素子。
［１１］ 前記燐光発光材料が下記一般式（Ｅ−１）で表されることを特徴とする［１０］に記載の有機電界発光素子。

（一般式（Ｅ−１）中、Ｚ¹及びＺ²はそれぞれ独立に、炭素原子又は窒素原子を表す。Ａ₁はＺ¹と窒素原子と共に５又は６員のヘテロ環を形成する原子群を表す。Ｂ₁はＺ²と炭素原子と共に５又は６員環を形成する原子群を表す。（Ｘ−Ｙ）はモノアニオン性の二座配位子を表す。ｎ_E1は１〜３の整数を表す。）
［１２］ 前記一般式（Ｅ−１）で表される燐光発光材料が下記一般式（Ｅ−２）で表されることを特徴とする［１１］に記載の有機電界発光素子。

（一般式（Ｅ−２）中、Ａ^E1〜Ａ^E8はそれぞれ独立に、窒素原子、または、Ｒ^Eで置換された炭素原子を表す。Ｒ^Eは水素原子又は置換基を表す。（Ｘ−Ｙ）はモノアニオン性の二座配位子を表す。ｎ_E2は１〜３の整数を表す。）
［１３］ 前記一般式（Ｅ−１）で表される燐光発光材料の極大発光波長が５００ｎｍ〜７００ｎｍであることを特徴とする［１１］または［１２］記載の有機電界発光素子。
［１４］ 前記有機層が、前記燐光発光材料を含む発光層とその他の有機層を有し、 前記発光層が前記一般式（１）で表される化合物を含有することを特徴とする［１０］〜［１３］のいずれか一項に記載の有機電界発光素子。
［１５］ 前記有機層が、前記燐光発光材料を含む発光層とその他の有機層を有し、
該その他の有機層が、前記発光層と前記陰極との間に配置されたホールブロック層を含み、且つ、該ホールブロック層が前記一般式（１）で表される化合物を含有することを特徴とする［１０］〜［１４］のいずれか一項に記載の有機電界発光素子。
［１６］ ［１０］〜［１５］のいずれか一項に記載の有機電界発光素子を用いたことを特徴とする発光装置、表示装置または照明装置。 [1] A charge transport material comprising a compound represented by the following general formula (1).

(In the general formula (1), X ¹⁰¹ represents a sulfur atom or an oxygen atom. R ¹⁰¹ and R ¹⁰² each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and these groups in .n101 which may be substituted represents an integer of 0 to 11, n102 represents an integer of 0 to 7, a plurality of R ¹⁰¹ and R ¹⁰² are optionally be the same or different .L ¹⁰¹ represents a single bond or Represents a divalent linking group, wherein any of R ¹⁰¹ , L ¹⁰¹ and R ¹⁰² represents a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group or silicon Including atom linking group.)
[2] The charge transport material according to [1], wherein the compound represented by the general formula (1) is represented by the following general formula (2).

(In the general formula (2), X ¹¹¹ represents a sulfur atom or an oxygen atom. R ¹¹¹ , R ¹¹² and R ¹¹³ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, N111 represents an integer of 0 to 11, n112 represents an integer of 0 to 7, n113 represents an integer of 0 to 4, and a plurality of R ¹¹¹ , R ¹¹² and R may be substituted with these groups. ¹¹³ may be the same or different, A ^{A1 to} A ^A5 each independently represent CH (the hydrogen atom of CH may be substituted with R ¹¹³ ) or a nitrogen atom, and m111 represents an integer of 0 to 6; represented. However, any of R ^111, R ¹¹² and R ^113, includes a fluorine atom, fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group or an aryl silyl group, n111, n112 Oyo n113 is not equal to 0 at the same time.)
[3] The charge transport material according to [2], wherein m111 in the general formula (2) is 1 to 5.
[4] The charge transport material according to any one of [1] to [3], wherein the compound represented by the general formula (1) is represented by the following general formula (3).

(In the general formula (3), X ¹²¹ represents a sulfur atom or an oxygen atom. R ¹²¹ , R ¹²² and R ¹²³ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group; N121 represents an integer of 0 to 11, n122 represents an integer of 0 to 7, n123 represents an integer of 0 to 4, and a plurality of R ¹²¹ , R ¹²² and R may be substituted with these groups. ¹²³ may be the same or different, and m121 represents an integer of 0 to 6. However, any one of R ¹²¹ , R ¹²² , and R ¹²³ represents a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, or an alkyl group. (Including silyl group or arylsilyl group, n121, n122 and n123 are not 0 at the same time.)
[5] The charge transport material according to any one of [1] to [4], wherein n101 in the general formula (1) is 0.
[6] The charge transport material according to any one of [1] to [5], wherein n102 in the general formula (1) is an integer of 0 to 2.
[7] The compound represented by the general formula (1) is composed of only carbon atoms and hydrogen atoms, excluding oxygen atoms and sulfur atoms in the dibenzothiophene skeleton and dibenzofuran skeleton. [6] The charge transport material according to any one of [6].
[8] The charge transport material according to any one of [1] to [7], wherein the compound represented by the general formula (1) includes a cycloalkyl group.
[9] The charge transport material according to any one of [1] to [8], wherein the compound represented by the general formula (1) has a molecular weight of 1200 or less.
[10] A substrate, a pair of electrodes disposed on the substrate and including an anode and a cathode, and an organic layer disposed between the electrodes, wherein the organic layer includes a phosphorescent material and [1] to [1] [9] An organic electroluminescent device comprising the charge transport material according to any one of [9].
[11] The organic electroluminescent element as described in [10], wherein the phosphorescent material is represented by the following general formula (E-1).

(In General Formula (E-1), Z ¹ and Z ² each independently represents a carbon atom or a nitrogen atom. A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle together with Z ¹ and the nitrogen atom. B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom, (XY) represents a monoanionic bidentate ligand, and n _E1 is an integer of 1 to 3. Represents.)
[12] The organic electroluminescent element as described in [11], wherein the phosphorescent material represented by the general formula (E-1) is represented by the following general formula (E-2).

(In the formula (E-2), the A ^E1 to A ^E8 each independently a nitrogen atom or,, .R ^E representing a carbon atom substituted with R ^E represents a hydrogen atom or a substituent. (X- Y) represents a monoanionic bidentate ligand, and n _E2 represents an integer of 1 to 3.)
[13] The organic electroluminescent element as described in [11] or [12], wherein the phosphorescent material represented by the general formula (E-1) has a maximum emission wavelength of 500 nm to 700 nm.
[14] The organic layer includes a light emitting layer containing the phosphorescent material and another organic layer, and the light emitting layer contains a compound represented by the general formula (1) [10] ] The organic electroluminescent element as described in any one of [13].
[15] The organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
The other organic layer includes a hole blocking layer disposed between the light emitting layer and the cathode, and the hole blocking layer contains the compound represented by the general formula (1). The organic electroluminescent element according to any one of [10] to [14].
[16] A light emitting device, a display device, or a lighting device using the organic electroluminescent element according to any one of [10] to [15].

  By using the compound represented by the general formula (1) in the present invention, it is possible to provide a charge transporting material and an organic electroluminescent device that have high efficiency and high driving durability after high-temperature storage and hardly cause dark spots.

It is the schematic which shows an example of a structure of the organic electroluminescent element which concerns on this invention. It is the schematic which shows an example of the light-emitting device which concerns on this invention. It is the schematic which shows an example of the illuminating device which concerns on this invention.

  Hereinafter, the contents of the present invention will be described in detail. The description of the constituent elements described below may be made based on typical embodiments of the present invention, but the present invention is not limited to such embodiments. In the present specification, “to” is used to mean that the numerical values described before and after it are included as a lower limit value and an upper limit value.

（一般式（１）において、Ｘ¹⁰¹は硫黄原子または酸素原子を表す。Ｒ¹⁰¹およびＲ¹⁰²はそれぞれ独立にアルキル基、アリール基、ヘテロアリール基、フッ素原子またはシリル基を表し、さらにこれらの基で置換されていてもよい。ｎ１０１は０〜１１の整数を表し、ｎ１０２は０〜７の整数を表し、複数のＲ¹⁰¹およびＲ¹⁰²は同一でも異なっていてもよい。Ｌ¹⁰¹は単結合または２価の連結基を表す。ただし、Ｒ¹⁰¹、Ｌ¹⁰¹およびＲ¹⁰²のいずれかは、フッ素原子、フルオロアルキル基、シクロアルキル基、シクロアルキレン基、シリル基、アルキルシリル基、アリールシリル基またはケイ素原子連結基を含む。）
本発明の電荷輸送材料はこのような構成を有することで、いかなる理論に拘泥するものでもないが、フッ素原子、フルオロアルキル基、シクロアルキル基、シクロアルキレン基、シリル基、アルキルシリル基、アリールシリル基またはケイ素原子連結基を導入することで分子間相互作用を適度に抑制させることができる。その結果、膜質の良好な膜が得られ、ダークスポットの発生を抑制することができる。また、本発明者らが検討した結果、これらの置換基は素子の効率や駆動耐久性を損なうことなく、有機膜のＴｇを高めることができる。そのため、本発明の電荷輸送材料を用いた有機電界発光素子は、高温保管後の効率や駆動耐久性にも優れる。 [Charge transport material]
The charge transport material of the present invention is characterized by comprising a compound represented by the following general formula (1).

(In the general formula (1), X ¹⁰¹ represents a sulfur atom or an oxygen atom. R ¹⁰¹ and R ¹⁰² each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and these groups in .n101 which may be substituted represents an integer of 0 to 11, n102 represents an integer of 0 to 7, a plurality of R ¹⁰¹ and R ¹⁰² are optionally be the same or different .L ¹⁰¹ represents a single bond or Represents a divalent linking group, wherein any of R ¹⁰¹ , L ¹⁰¹ and R ¹⁰² represents a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group or silicon Including atom linking group.)
The charge transport material of the present invention is not limited to any theory by having such a structure, but is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group. By introducing a group or a silicon atom linking group, the intermolecular interaction can be moderately suppressed. As a result, a film with good film quality can be obtained, and generation of dark spots can be suppressed. Further, as a result of investigations by the present inventors, these substituents can increase the Tg of the organic film without impairing the efficiency and driving durability of the element. Therefore, the organic electroluminescent element using the charge transport material of the present invention is excellent in efficiency after high temperature storage and driving durability.

  The charge transport material of the present invention represented by the general formula (1) is preferably used for organic electronic elements such as electrophotography, organic transistors, organic photoelectric conversion elements (energy conversion applications, sensor applications, etc.), organic electroluminescence elements and the like. It is particularly preferable to use it for an organic electroluminescent device.

  The charge transport material of the present invention can also be used for a thin film containing the compound represented by the general formula (1). The thin film can be formed using the composition by a dry film forming method such as an evaporation method or a sputtering method, or a wet film forming method such as a transfer method or a printing method. The thickness of the thin film may be any thickness depending on the application, but is preferably 0.1 nm to 1 mm, more preferably 0.5 nm to 1 μm, still more preferably 1 nm to 200 nm, and particularly preferably 1 nm to 100 nm. is there.

Hereinafter, the preferable range of the charge transport material comprising the compound represented by the general formula (1) will be described.
In the present invention, the hydrogen atom (H) in the description of the general formula (1) includes an isotope (deuterium atom (D)), and the atoms constituting the substituent further include the isotope. Represents that
In the present invention, when referred to as “substituent”, the substituent may be substituted. For example, the term “alkyl group” in the present invention includes an alkyl group substituted with a fluorine atom (for example, trifluoromethyl group) and an alkyl group substituted with an aryl group (for example, triphenylmethyl group). When the term “alkyl group having 1 to 6 carbon atoms” is used, it means that the number of carbon atoms is 1 to 6 as all groups including those substituted.
In the present invention, a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group or a silicon atom linking group is also referred to as a “specific substituent”.
However, in the present specification, the “cycloalkylene group” means a generic name such as 1,4-cyclohexanediyl, 1,3-cyclohexanediyl, 1,2-cyclohexanediyl, cyclopentane, and the like. It does not mean a ring with one atom removed.

In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom. A sulfur atom having a large van der Faals radius is preferred from the viewpoint of improving electron mobility.

In the general formula (1), R ¹⁰¹ and R ¹⁰² each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be further substituted with these groups.

When R ¹⁰¹ and R ¹⁰² are alkyl groups, the alkyl group may be linear, branched or cyclic, and generally has 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms. More preferably, it is an alkyl group having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and most preferably 1 to 4 carbon atoms. For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, n -Octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, and the like, methyl group, ethyl group, n-propyl group, n-butyl group, t-butyl group, cyclopentyl Group and cyclohexyl group are preferred, more preferably methyl group, t-butyl group, cyclopentyl group and cyclohexyl group, particularly preferably cyclopentyl group and cyclohexyl group, and most preferably cyclohexyl group.

The alkyl group as R ¹⁰¹ and R ¹⁰² may further have an alkyl group, aryl group, heteroaryl group, fluorine atom or silyl group as a substituent. Among them, it is preferably substituted with a fluorine atom, more preferably all hydrogen atoms are substituted with fluorine atoms to form a perfluoroalkyl group, and particularly preferably a trifluoromethyl group.

When R ¹⁰¹ and R ¹⁰² are silyl groups, the silyl group is preferably substituted, and the substituent is preferably an alkyl group or an aryl group. When the silyl group as R ¹⁰¹ and R ¹⁰² is substituted with an alkyl group or an aryl group, all hydrogen atoms are substituted with an alkyl group or an aryl group to form a trialkylsilyl group or a triarylsilyl group. Is more preferable, and it is particularly preferable to form a trimethylsilyl group or a triphenylsilyl group.

When R ¹⁰¹ and R ¹⁰² are heteroaryl groups, the heteroaryl group is preferably a 5- or 6-membered heterocycle containing a nitrogen atom. Examples of the 5- or 6-membered heterocycle containing a nitrogen atom include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, a triazole ring, an oxadiazole ring, and a thiadiazole ring. Is mentioned. When the charge transport material of the present invention is used in an organic electroluminescence device, among these, from the viewpoints of stability, emission wavelength control and emission quantum yield, among them, a pyridine ring, a pyrazine ring, an imidazole ring, and a pyrazole ring are more preferable. Particularly preferred are a pyridine ring, an imidazole ring and a pyrazine ring, more preferred are a pyridine ring and an imidazole ring, and most preferred is a pyridine ring.

When R ¹⁰¹ and R ¹⁰² are aryl groups, they preferably have 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, naphthyl, anthryl and the like. It is done. R ¹⁰¹ is preferably a monocyclic aryl group, and more preferably a phenyl group. On the other hand, R ¹⁰² may be either a monocyclic aryl group or an aryl group having a condensed ring, and in the case of a monocyclic aryl group, it is preferably a phenyl group, and in the case of an aryl group having a condensed ring, triphenylene. It is preferably a group. The triphenylene group in the case of R ¹⁰² may further have a substituent, and its preferred range is the same as the preferred range of R ¹⁰¹ .

The aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² may further have an alkyl group, aryl group, heteroaryl group, fluorine atom or silyl group as a substituent.
When the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² is substituted with an alkyl group, a fluorine atom or a silyl group, the preferred range of the alkyl group, heteroaryl group, fluorine atom or silyl group as the substituent is , R ¹⁰¹ and R ¹⁰² are the same as when an alkyl group, a heteroaryl group, a fluorine atom or a silyl group. When the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² is substituted with an alkyl group, heteroaryl group, fluorine atom or silyl group, the number of these substituents is the aryl group as R ¹⁰¹ and R ¹⁰² or The number is preferably 1 to 3 with respect to the heteroaryl group, more preferably 1 or 2, and particularly preferably 1.
When the aryl group or heteroaryl group is substituted with respect to the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² , the aryl group and arylene group, or the heteroaryl group and heteroarylene group formed by the substitution are These are preferably monocyclic, more preferably 6-membered monocyclic.

With respect to the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² , an aryl group or heteroaryl group is substituted to form a 6-membered monocyclic aryl group and arylene group, or heteroaryl group and heteroaryl group. When the arylene group or these linking groups and substituents are connected in combination with each other, a monovalent substituent in which a single ring of these 6-membered rings is connected by a single bond (6-membered connected by a single bond). The number of monocyclic rings is preferably 3 or less, more preferably 1 or 2. For example, preferred structures in the case where a 6-membered monocyclic aryl group and an arylene group form a linking substituent include a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a kinkphenyl group, and the like. It is done. Among these, any of a phenyl group, a biphenyl group, and a terphenyl group (particularly 3,5-diphenylphenyl) is preferable, and either a phenyl group or a biphenyl group is more preferable, and a phenyl group is most preferable. The above example has the same structure when a heteroaryl group and a heteroarylene group are linked.

At this time, R ¹⁰¹ is particularly preferably the following linking substituent (R ¹⁰¹ ).

（上記式中、Ａ^A11〜Ａ^A20はそれぞれ独立にＣＨ（ＣＨの水素原子は置換されていてもよい）または窒素原子を表し、ｍ２０１は０〜２の整数を表す。但し、Ａ^A11〜Ａ^A20で表される６員環の単環であるアリール基とアリーレン基、または、ヘテロアリール基とヘテロアリーレン基は、さらなる置換基としてアリール基またはヘテロアリール基を有さない。Ｒ²⁰¹およびＲ²⁰²はそれぞれ独立にアルキル基、フッ素原子またはシリル基を表す。ｎ２０１は０〜５の整数を表す。ｎ２０２は０〜４の整数を表す。＊はトリフェニレン環への結合部位を表す。）
連結置換基（Ｒ¹⁰¹）中、Ａ^A11〜Ａ^A20でそれぞれ表される６員環の単環であるアリール基とアリーレン基、または、ヘテロアリール基とヘテロアリーレン基、あるいはそれらの基の組み合わせの好ましい範囲は、さらなる置換基としてアリール基またはヘテロアリール基を有さない以外は、前記一般式（１）におけるＲ¹⁰¹およびＲ¹⁰²としてのアリール基またはヘテロアリール基の好ましい範囲と同様である。
連結置換基（Ｒ¹⁰¹）中、Ｒ²⁰¹とＲ²⁰²の好ましい範囲は、前記一般式（１）におけるＲ¹⁰¹およびＲ¹⁰²としてのアルキル基、フッ素原子またはシリル基の好ましい範囲と同様である。
連結置換基（Ｒ¹⁰¹）中、ｍ２０１の好ましい範囲は０または１であり、より好ましくは０である。
連結置換基（Ｒ¹⁰¹）中、Ｒ²⁰¹およびＲ²⁰²がアルキル基またはシリル基である場合のｎ２０１およびｎ２０２の好ましい範囲はそれぞれ独立に０〜２であり、より好ましくは０または１である。Ｒ²⁰¹およびＲ²⁰²がフッ素原子である場合のｎ２０１およびｎ２０２の好ましい範囲はそれぞれ独立に０〜３であり、より好ましくは０〜２であり、特に好ましくは０または１である。ｎ２０１およびｎ２０２の合計の好ましい範囲は、ｎ１０１の好ましい範囲と同様である。

(In the above formula, A ^{A11 to} A ^A20 each independently represent CH (the hydrogen atom of CH may be substituted) or a nitrogen atom, and m201 represents an integer of 0 to 2. However, A ^{A11 to} A ^The aryl group and the arylene group, or the heteroaryl group and the heteroarylene group, which are monocycles of the 6-membered ring represented by ^A20 , do not have an aryl group or a heteroaryl group as a further substituent R ²⁰¹ and R ²⁰² Each independently represents an alkyl group, a fluorine atom or a silyl group, n201 represents an integer of 0 to 5, n202 represents an integer of 0 to 4, and * represents a bonding site to a triphenylene ring.)
In the linking substituent (R ¹⁰¹ ), an aryl group and an arylene group, or a heteroaryl group and a heteroarylene group, or a combination of these groups, each of which is a monocyclic 6-membered ring represented by A ^{A11 to} A ^A20 The preferred range is the same as the preferred range of the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² in the general formula (1) except that the aryl group or heteroaryl group does not have an additional substituent.
In the linking substituent (R ¹⁰¹ ), the preferred range of R ²⁰¹ and R ^{202 is the same as} the preferred range of the alkyl group, fluorine atom or silyl group as R ¹⁰¹ and R ¹⁰² in the general formula (1).
In the linking substituent (R ¹⁰¹ ), the preferred range for m201 is 0 or 1, more preferably 0.
In the linking substituent (R ¹⁰¹ ), when R ²⁰¹ and R ²⁰² are an alkyl group or a silyl group, preferred ranges of n201 and n202 are each independently 0 to 2, more preferably 0 or 1. When R ²⁰¹ and R ²⁰² are fluorine atoms, the preferable range of n201 and n202 is each independently 0 to 3, more preferably 0 to 2, particularly preferably 0 or 1. The preferable range of the total of n201 and n202 is the same as the preferable range of n101.

When m201 in the linking substituent (R ¹⁰¹ ) is 2 or more, the repeating units represented by m201 may be the same or different.

R ¹⁰¹ in the general formula (1) is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group, or a silicon atom linking group (the specific substituent). Any embodiment may be included, but in the present invention, an embodiment in which R ¹⁰¹ in the general formula (1) includes a fluorine atom, a fluoroalkyl group, or an alkylsilyl group is preferable, and an embodiment in which none of these specific substituents is included. Is more preferable.

Next, R ¹⁰² is particularly preferably the following linking substituent (R ¹⁰² ).

（上記式中、Ａ^A21〜Ａ^A30はそれぞれ独立にＣＨ（ＣＨの水素原子は置換されていてもよい）または窒素原子を表し、ｍ３０１は０〜３の整数を表す。但し、Ａ^A21〜Ａ^A30で表される６員環の単環であるアリール基とアリーレン基、または、ヘテロアリール基とヘテロアリーレン基は、さらなる置換基としてアリール基またはヘテロアリール基を有さない。Ｒ³⁰¹およびＲ³⁰²はそれぞれ独立にアルキル基、フッ素原子またはシリル基を表す。ｎ３０１は０〜５の整数を表す。ｎ３０２は０〜４の整数を表す。＊はジベンゾチオフェンまたはジベンゾフラン構造への結合部位を表す。）
連結置換基（Ｒ¹⁰²）中、Ａ^A21〜Ａ^A30で表される６員環の単環であるアリール基とアリーレン基、または、ヘテロアリール基とヘテロアリーレン基の好ましい範囲は、さらなる置換基としてアリール基またはヘテロアリール基を有さない以外は、前記一般式（１）におけるＲ¹⁰¹およびＲ¹⁰²としてのアリール基またはヘテロアリール基の好ましい範囲と同様である。
連結置換基（Ｒ¹⁰²）中、Ｒ³⁰¹とＲ³⁰²の好ましい範囲は、前記一般式（１）におけるＲ¹⁰¹およびＲ¹⁰²としてのアルキル基、フッ素原子またはシリル基の好ましい範囲と同様である。
連結置換基（Ｒ¹⁰²）中、ｍ３０１の好ましい範囲は０〜２の整数であり、より好ましくは０または１であり、特に好ましくは０である。
連結置換基（Ｒ¹⁰²）中、Ｒ³⁰¹およびＲ³⁰²がアルキル基またはシリル基である場合のｎ３０１およびｎ３０２の好ましい範囲はそれぞれ独立に０〜２であり、より好ましくは０または１である。Ｒ³⁰¹およびＲ³⁰²がフッ素原子である場合のｎ３０１およびｎ３０２の好ましい範囲はそれぞれ独立に０〜３であり、より好ましくは０〜２であり、特に好ましくは０または１である。ｎ３０１およびｎ３０２の合計の好ましい範囲は、ｎ１０２の好ましい範囲と同様である。

(In the above formula, A ^{A21 to} A ^A30 each independently represent CH (the hydrogen atom of CH may be substituted) or a nitrogen atom, and m301 represents an integer of 0 to 3. However, A ^{A21 to} A ^The aryl group and the arylene group, or the heteroaryl group and the heteroarylene group, which are monocycles of the six-membered ring represented by ^A30 , do not have an aryl group or a heteroaryl group as a further substituent R ³⁰¹ and R ³⁰² Each independently represents an alkyl group, a fluorine atom or a silyl group, n301 represents an integer of 0 to 5, n302 represents an integer of 0 to 4, and * represents a binding site to a dibenzothiophene or dibenzofuran structure.
The preferred range of the aryl group and arylene group, or the heteroaryl group and heteroarylene group, which are monocyclic 6-membered rings represented by A ^{A21 to} A ^A30 in the linking substituent (R ¹⁰² ), is as a further substituent. except that no aryl group or heteroaryl group is the same as the preferred range of aryl or heteroaryl group as R ¹⁰¹ and R ¹⁰² in formula (1).
In the linking substituent (R ¹⁰² ), the preferred ranges of R ³⁰¹ and R ³⁰² are the same as the preferred ranges of the alkyl group, fluorine atom or silyl group as R ¹⁰¹ and R ¹⁰² in the general formula (1).
In the linking substituent (R ¹⁰² ), a preferable range of m301 is an integer of 0 to 2, more preferably 0 or 1, and particularly preferably 0.
In the linking substituent (R ¹⁰² ), when R ³⁰¹ and R ³⁰² are an alkyl group or a silyl group, preferred ranges of n301 and n302 are each independently 0 to 2, more preferably 0 or 1. When R ³⁰¹ and R ³⁰² are fluorine atoms, the preferred range of n ³⁰¹ and n ³⁰² is independently 0 to 3, more preferably 0 to 2, particularly preferably 0 or 1. The preferable range of the total of n301 and n302 is the same as the preferable range of n102.

When m301 in the linked substituent (R ¹⁰² ) is 2 or more, the repeating units represented by m301 may be the same or different. Among them, it is preferable that the repeating units represented by m301 are different from each other. In that case, the heteroarylene group and the arylene group are more preferably bonded in this order from the binding site to the dibenzothiophene or dibenzofuran structure. preferable.

R ¹⁰² in the general formula (1) is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group, or a silicon atom linking group (the specific substituent). Any embodiment may be included, but in the present invention, an embodiment in which R ¹⁰² in the general formula (1) includes a fluorine atom, a fluoroalkyl group, a cycloalkyl group, or an alkylsilyl group is preferable, and a cycloalkyl group, an alkylsilyl group, or An embodiment containing an arylsilyl group is more preferred, and an embodiment containing a cycloalkyl group is particularly preferred.

In the linking substituent (R ¹⁰¹ ) and the linking substituent (R ¹⁰² ), the number of 6-membered monocycles linked at the para position is preferably 3 or less. For example, when a 6-membered monocycle is further linked to the end of the p-terphenylene group, it is preferably linked at the meta position or ortho position, and more preferably linked at the meta position.
The preferred range of the number of the 6-membered monocycles linked at the para position is the same for L ₁₀₁ described later.

In the general formula (1), n101 represents an integer of 0 to 11, preferably an integer of 0 to 2, particularly preferably 0 or 1, and more preferably 0.
In the general formula (1), when n101 is not 0, the position where the R ¹⁰¹ is substituted with the triphenylene ring structure is not particularly limited, but in the general formula (1), the triphenylene ring is connected to the linking group L ^101. It preferably has a substituent R ^{101 in} addition to the ring.

In the general formula (1), n102 represents an integer of 0 to 7, preferably an integer of 0 to 2, particularly preferably 0 or 1, and more preferably 0.
In the general formula (1), when n102 is not 0, the position at which the R ¹⁰² is substituted with a dibenzothiophene or dibenzofuran structure is not particularly limited, but the dibenzothiophene or dibenzofuran structure is a linking group in the general formula (1). In addition to the ring connected to L ¹⁰¹ , it preferably has a substituent R ¹⁰² .

In the general formula (1), L ¹⁰¹ represents a single bond or a divalent linking group. The preferred range of L ¹⁰¹ is not particularly limited, and examples thereof include a single bond or any divalent linking group. Among them, a single bond, an alkylene group, or a silicon atom linking group, an arylene group, an aryl group, or a combination thereof is preferable, and a linking group represented by the general formula (2) described later is more preferable. . In addition, when L ¹⁰¹ is an alkylene group, the alkylene group may have a substituent, and it is particularly preferable that substituents of the alkylene group are linked to form a cycloalkylene group.

In the general formula (1), any one of R ¹⁰¹ , L ¹⁰¹ and R ¹⁰² is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group, or a silicon atom linkage A group (the specific substituent). That is, when R ¹⁰¹ and R ¹⁰² do not contain the specific substituent, L ¹⁰¹ contains the specific substituent.
L ¹⁰¹ in the general formula (1) is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group or a silicon atom linking group (the specific substituent). In the present invention, L ¹⁰¹ in the general formula (1) is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, an alkylsilyl group, an arylsilyl group, An embodiment containing a silicon atom linking group is preferred, an embodiment containing a fluorine atom, a fluoroalkyl group or a cycloalkyl group is more preferred, and an embodiment containing a cycloalkyl group is particularly preferred.

  In the charge transport material of the present invention, the compound represented by the general formula (1) is preferably represented by the following general formula (2).

（一般式（２）において、Ｘ¹¹¹は硫黄原子または酸素原子を表す。Ｒ¹¹¹、Ｒ¹¹²およびＲ¹¹³はそれぞれ独立にアルキル基、アリール基、ヘテロアリール基、フッ素原子またはシリル基を表し、さらにこれらの基で置換されていてもよい。ｎ１１１は０〜１１の整数を表し、ｎ１１２は０〜７の整数を表し、ｎ１１３は０〜４の整数を表し、複数のＲ¹¹¹、Ｒ¹¹²およびＲ¹¹³は同一でも異なっていてもよい。Ａ^A1〜Ａ^A5はそれぞれ独立にＣＨ（ＣＨの水素原子はＲ¹¹³で置換されていてもよい）または窒素原子を表し、ｍ１１１は０〜６の整数を表す。ただし、Ｒ¹¹¹、Ｒ¹¹²およびＲ¹¹³のいずれかは、フッ素原子、フルオロアルキル基、シクロアルキル基、シリル基、アルキルシリル基またはアリールシリル基を含み、ｎ１１１、ｎ１１２およびｎ１１３が同時に０になることはない。）

(In the general formula (2), X ¹¹¹ represents a sulfur atom or an oxygen atom. R ¹¹¹ , R ¹¹² and R ¹¹³ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, N111 represents an integer of 0 to 11, n112 represents an integer of 0 to 7, n113 represents an integer of 0 to 4, and a plurality of R ¹¹¹ , R ¹¹² and R may be substituted with these groups. ¹¹³ may be the same or different, A ^{A1 to} A ^A5 each independently represent CH (the hydrogen atom of CH may be substituted with R ¹¹³ ) or a nitrogen atom, and m111 represents an integer of 0 to 6; represented. However, any of R ^111, R ¹¹² and R ^113, includes a fluorine atom, fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group or an aryl silyl group, n111, n112 Oyo n113 is not equal to 0 at the same time.)

The preferred ranges of X ¹¹¹ , R ¹¹¹ , R ¹¹² , n111 and n112 in the general formula (2) are the same as the preferred ranges of X ¹⁰¹ , R ¹⁰¹ , R ¹⁰² , n101 and n102 in the general formula (1), respectively. is there.

A preferred range of an arylene group, a heteroarylene group, or a combination thereof, which is a monocyclic 6-membered ring represented by A ^{A1 to} A ^A5 in the general formula (2), R in the general formula (1) ^This is the same as the preferred range of the aryl group or heteroaryl group as ¹⁰¹ and ^R102 .

  M111 in the general formula (2) is 0 to 6, preferably 1 to 6, more preferably 1 to 5, and particularly preferably 1 to 4.

R ¹¹³ in the general formula (2) independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be further substituted with these groups. Examples of the alkyl group, aryl group, heteroaryl group, fluorine atom or silyl group as R ¹¹³ in the general formula (2) are the same as the examples of R ^{202 in} the linked substituent (R ¹⁰¹ ).
R ¹¹³ in the general formula (2) preferably contains a fluorine atom, a fluoroalkyl group, a cycloalkyl group, an alkylsilyl group or an arylsilyl group, and more preferably contains a fluorine atom, a fluoroalkyl group or a cycloalkyl group. In particular, it preferably contains a cycloalkyl group. The preferred range of each of these substituents is the same as the preferred range of each substituent listed for R ¹⁰¹ in the general formula (1).

N113 in the general formula (2) represents an integer of 0 to 4, preferably when R ¹¹³ is a fluorine atom is 0-3, more preferably 0-2, 0 or 1 It is particularly preferred. When R ¹¹³ is an alkyl group, it is preferably 0 to 2, more preferably 0 or 1, and particularly preferably 0. When R ²⁰¹ and R ²⁰² are an aryl group, a heteroaryl group, a fluoroalkyl group, an alkylsilyl group, or an arylsilyl group, it is preferably 0 or 1, more preferably 0. When R ¹¹³ is a cycloalkyl group, it is preferably 0 or 1, and more preferably 1.

When m111 in the general formula (2) is 2 or more, the repeating units represented by m111 may be the same or different.
The repeating unit represented by m111 may have the above-mentioned preferable number of R ¹¹³ in each repeating unit, but in the entire repeating unit represented by m111, that is, the general formula (1) The number of specific substituents in the entire L ^{111 in} the formula is preferably 0 to 3, more preferably 0 to 2, and particularly preferably 0 or 1 when R ¹¹³ is a fluorine atom. . When R ¹¹³ is an alkyl group, it is preferably 0 to 2, more preferably 0 or 1, and particularly preferably 0. When R ²⁰¹ and R ²⁰² are an aryl group, a heteroaryl group, a fluoroalkyl group, an alkylsilyl group, or an arylsilyl group, it is preferably 0 or 1, more preferably 0. When R ¹¹³ is a cycloalkyl group, it is preferably 0 or 1, and more preferably 1.
repeating unit represented by m111 has a R ¹¹³ of the number of the abovementioned preferred ranges in each repeating unit, has a R ¹¹³ of the number of the above-mentioned preferred range in the whole repeating unit represented by m111 It is preferable. However, this is not the case when the specific substituent is a fluorine atom.

  In the charge transport material of the present invention, the compound represented by the general formula (1) is preferably represented by the following general formula (3).

（一般式（３）において、Ｘ¹²¹は硫黄原子または酸素原子を表す。Ｒ¹²¹、Ｒ¹²²およびＲ¹²³はそれぞれ独立にアルキル基、アリール基、ヘテロアリール基、フッ素原子またはシリル基を表し、さらにこれらの基で置換されていてもよい。ｎ１２１は０〜１１の整数を表し、ｎ１２２は０〜７の整数を表し、ｎ１２３は０〜４の整数を表し、複数のＲ¹²¹、Ｒ¹²²およびＲ¹²³は同一でも異なっていてもよい。ｍ１２１は０〜６の整数を表す。ただし、Ｒ¹²¹、Ｒ¹²²、Ｒ¹²³のいずれかは、フッ素原子、フルオロアルキル基、シクロアルキル基、シリル基、アルキルシリル基またはアリールシリル基を含み、ｎ１２１、ｎ１２２およびｎ１２３が同時に０になることはない。）

(In the general formula (3), X ¹²¹ represents a sulfur atom or an oxygen atom. R ¹²¹ , R ¹²² and R ¹²³ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group; N121 represents an integer of 0 to 11, n122 represents an integer of 0 to 7, n123 represents an integer of 0 to 4, and a plurality of R ¹²¹ , R ¹²² and R may be substituted with these groups. ¹²³ may be the same or different, and m121 represents an integer of 0 to 6. However, any one of R ¹²¹ , R ¹²² , and R ¹²³ represents a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, or an alkyl group. (Including silyl group or arylsilyl group, n121, n122 and n123 are not 0 at the same time.)

The preferred ranges of X ¹²¹ , R ¹²¹ , R ¹²² , n121 and n122 in the general formula (3) are the same as the preferred ranges of X ¹⁰¹ , R ¹⁰¹ , R ¹⁰² , n101 and n102 in the general formula (1), respectively. is there.
The preferable ranges of R ¹²³ , m121 and n123 in the general formula (3) are the same as the preferable ranges of R ¹¹³ , m111 and n113 in the general formula (2), respectively.

（一般式（６）において、Ｘ⁶は硫黄原子または酸素原子を表す。ｍ６は１〜６の整数を表す。Ｒ⁶は、アルキル基、アリール基、ヘテロアリール基、フッ素原子またはシリル基を表す。ｎ６は０〜４の整数を表す。但し、ｍ６×ｎ６個のＲ⁶の内、少なくとも一つはフッ素原子、フルオロアルキル基、シクロアルキル基、シリル基、アルキルシリル基またはアリールシリル基である。） In the charge transport material of the present invention, the compound represented by the general formula (3) is preferably represented by the following general formula (6).

(In General Formula (6), X ⁶ represents a sulfur atom or an oxygen atom. M6 represents an integer of 1 to ^6. R ⁶ represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, or a silyl group. N6 represents an integer of 0 to 4, provided that at least one of m6 × n6 R ⁶ is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group or an arylsilyl group. .)

The preferable range of X ⁶ in the general formula (6) is the same as the preferable range of X ¹⁰¹ in the general formula (1). The preferred ranges of R ⁶ and n6 in the general formula (6) are the same as the preferred ranges of R ¹¹³ and n113 in the general formula (2), respectively. m6 represents an integer of 1 to 6. m6 is preferably 0 to 2, more preferably 0 or 1. However, at least one of m6 × n6 R ⁶ is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, or an arylsilyl group.

  The compound represented by the general formula (1) is more preferably composed of only carbon atoms and hydrogen atoms, excluding oxygen atoms and sulfur atoms in the dibenzothiophene skeleton and dibenzofuran skeleton. Moreover, it is more preferable that the compound represented by the general formula (1) includes a cycloalkyl group.

The T ₁ energy in the film state of the compound represented by the general formula (1) is preferably 2.39 eV (55.0 kcal / mol) or more and 3.25 eV (75.0 kcal / mol) or less. It is more preferable that it is 0.47 eV (57.0 kcal / mol) or more and 3.04 eV (70.0 kcal / mol) or less, and 2.52 eV (58.0 kcal / mol) or more and 2.82 eV (65.0 kcal / mol) or less. More preferably. In particular, when a phosphorescent light emitting material is used as the light emitting material, the T ₁ energy is preferably in the above range.

The T ₁ energy can be obtained from the short wavelength end of a phosphorescence emission spectrum of a thin film of material. For example, a material is deposited on a cleaned quartz glass substrate to a film thickness of about 50 nm by a vacuum deposition method, and the phosphorescence emission spectrum of the thin film is F-7000 Hitachi Spectrofluorimeter (Hitachi High-Technologies) under liquid nitrogen temperature. Use to measure. T ₁ energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.

  In the charge transport material of the present invention, the molecular weight of the compound represented by the general formula (1) is preferably 1200 or less, more preferably 1000 or less, and further preferably 500 or more and 1000 or less. It is particularly preferably 550 or more and 900 or less, and most preferably 600 or more and 850 or less. By setting the molecular weight within this range, a material having good film quality and excellent sublimation purification / deposition suitability can be obtained.

  The glass transition temperature (Tg) of the compound represented by the general formula (1) is 80 ° C. or higher and 400 ° C. or lower from the viewpoint of stably operating the organic electroluminescent device against heat generated during high temperature driving or driving the device. Preferably, the temperature is 100 ° C. or higher and 400 ° C. or lower, more preferably 120 ° C. or higher and 400 ° C. or lower.

  Specific examples of the compound represented by the general formula (1) are shown below, but the present invention is not limited thereto.

The compound represented by the above general formula (1) is disclosed in JP 2004-43349 A, JP 2004-83481 A, US 2006/0280965, WO 2009/021107, JP 2009-111068 A, and Special Table 2010-535809. It can synthesize | combine combining the method as described in gazette etc., and other well-known reaction.
After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

（一般式（１）において、Ｘ¹⁰¹は硫黄原子または酸素原子を表す。Ｒ¹⁰¹およびＲ¹⁰²はそれぞれ独立にアルキル基、アリール基、ヘテロアリール基、フッ素原子またはシリル基を表し、さらにこれらの基で置換されていてもよい。ｎ１０１は０〜１１の整数を表し、ｎ１０２は０〜７の整数を表し、複数のＲ¹⁰¹およびＲ¹⁰²は同一でも異なっていてもよい。Ｌ¹⁰¹は単結合または２価の連結基を表す。ただし、Ｒ¹⁰¹、Ｌ¹⁰¹およびＲ¹⁰²のいずれかは、フッ素原子、フルオロアルキル基、シクロアルキル基、シクロアルキレン基、シリル基、アルキルシリル基、アリールシリル基またはケイ素原子連結基を含む。） [Organic electroluminescence device]
The organic electroluminescent element of the present invention has a substrate, a pair of electrodes including an anode and a cathode disposed on the substrate, and an organic layer disposed between the electrodes, and the organic layer emits phosphorescence. It contains the material and the charge transport material of the present invention, that is, the compound represented by the general formula (1).

(In the general formula (1), X ¹⁰¹ represents a sulfur atom or an oxygen atom. R ¹⁰¹ and R ¹⁰² each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and these groups in .n101 which may be substituted represents an integer of 0 to 11, n102 represents an integer of 0 to 7, a plurality of R ¹⁰¹ and R ¹⁰² are optionally be the same or different .L ¹⁰¹ represents a single bond or Represents a divalent linking group, wherein any of R ¹⁰¹ , L ¹⁰¹ and R ¹⁰² represents a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group or silicon Including atom linking group.)

The structure of the organic electroluminescent element of the present invention is not particularly limited. FIG. 1 shows an example of the configuration of the organic electroluminescent element of the present invention. 1 has an organic layer on a substrate 2 between a pair of electrodes (anode 3 and cathode 9).
The element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.
Hereinafter, the preferable aspect of the organic electroluminescent element of this invention is demonstrated in detail in order of a board | substrate, an electrode, an organic layer, a protective layer, a sealing container, a drive method, light emission wavelength, and a use.

<Board>
The organic electroluminescent element of the present invention has a substrate.
The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.

<Electrode>
The organic electroluminescent element of the present invention is disposed on the substrate and has a pair of electrodes including an anode and a cathode.
In view of the properties of the light-emitting element, at least one of the pair of electrodes, the anode and the cathode, is preferably transparent or translucent.

(anode)
The anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials. As described above, the anode is usually provided as a transparent anode.

(cathode)
The cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element. The electrode material can be selected as appropriate.

<Organic layer>
The organic electroluminescent element of the present invention has an organic layer disposed between the electrodes, and the organic layer includes a phosphorescent material and a compound represented by the general formula (1).
There is no restriction | limiting in particular in the said organic layer, Although it can select suitably according to the use and objective of an organic electroluminescent element, It is preferable to form on the said transparent electrode or the said semi-transparent electrode. In this case, the organic layer is formed on the entire surface or one surface of the transparent electrode or the semitransparent electrode.
There is no restriction | limiting in particular about the shape of a organic layer, a magnitude | size, thickness, etc., According to the objective, it can select suitably.
Hereinafter, in the organic electroluminescent element of the present invention, the configuration of the organic layer, the method for forming the organic layer, preferred embodiments of the layers constituting the organic layer, and materials used for the layers will be described in order.

(Organic layer structure)
In the organic electroluminescent element of the present invention, the organic layer preferably includes a charge transport layer. The charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element. Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer. If the charge transport layer is a hole injection layer, a hole transport layer, an electron block layer, or a light emitting layer, a low-cost and highly efficient organic electroluminescent device can be produced.
The organic electroluminescent element of the present invention preferably has a light emitting layer containing the phosphorescent material and another organic layer, and the light emitting layer contains the compound represented by the general formula (1). Furthermore, in the organic electroluminescent element of the present invention, it is more preferable that the organic layer has a light emitting layer containing the phosphorescent material and another organic layer. However, in the organic electroluminescent element of the present invention, even when the organic layer has a light emitting layer and other organic layers, the layers do not necessarily have to be clearly distinguished.

  In the organic electroluminescent element of the present invention, the organic layer contains a phosphorescent material and a compound represented by the general formula (1). At this time, there is no particular limitation on the place where the phosphorescent material and the compound represented by the general formula (1) are included. In this invention, it is more preferable that the said organic layer has the light emitting layer containing the said phosphorescence-emitting material, and another organic layer, and the said light emitting layer contains the compound represented by the said General formula (1). At this time, it is preferable that the compound represented by the general formula (1) is used as a host material of the light emitting layer (hereinafter also referred to as a host compound).

The compound represented by the general formula (1) may be contained in any organic layer between the cathode and the anode of the organic electroluminescence device.
The organic layer that may contain the compound represented by the general formula (1) includes a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block. Layer (a hole block layer, an electron block layer, etc.), etc., preferably a light emitting layer, an exciton block layer, a charge block layer, an electron transport layer, an electron injection layer, more preferably A light emitting layer, an exciton blocking layer, a charge blocking layer, or an electron transporting layer, more preferably a light emitting layer or a hole blocking layer.

  When the compound represented by the general formula (1) is contained in the light emitting layer, the compound is preferably contained in an amount of 0.1 to 99% by mass, and 1 to 95% by mass with respect to the total mass of the light emitting layer. Is more preferable, and it is more preferable that 10-95 mass% is contained.

  The maximum emission wavelength of the light emitting material using the compound represented by the general formula (1) is preferably 400 to 700 nm, more preferably 500 to 700 nm, and further preferably 520 to 650 nm, Most preferably, it is 520-550 nm.

Further, the electron transporting layer or the hole blocking layer (more preferably, a hole blocking layer) is provided between the pair of electrodes, and the electron transporting layer or the hole blocking layer is represented by the general formula (1). It is also preferable to contain a compound to be prepared.
When the compound represented by the general formula (1) is contained in an organic layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, and 85 to 100% by mass with respect to the total mass of the organic layer. More preferably it is included.

  A plurality of these organic layers may be provided, and when a plurality of layers are provided, they may be formed of the same material, or may be formed of different materials for each layer.

(Formation method of organic layer)
In the organic electroluminescence device of the present invention, each organic layer is formed by a dry film forming method such as a vapor deposition method or a sputtering method, a wet film forming method such as a transfer method, a printing method, a spin coating method, or a bar coating method (solution coating method). Any of these can be suitably formed.
In the organic electroluminescent element of the present invention, the organic layer disposed between the pair of electrodes includes at least one layer formed by vapor deposition of a composition containing the compound represented by the general formula (1). Is preferred.

(Light emitting layer)
The light emitting layer receives holes from the anode, hole injection layer or hole transport layer and receives electrons from the cathode, electron injection layer or electron transport layer when an electric field is applied, and provides a field for recombination of holes and electrons. And a layer having a function of emitting light. However, the light emitting layer in the present invention is not necessarily limited to light emission by such a mechanism. The light emitting layer in the organic electroluminescent element of the present invention preferably contains at least one phosphorescent material.

  The light emitting layer in the organic electroluminescent element of the present invention may be composed of only the light emitting material, or may be a mixed layer of a host material and the light emitting material. The kind of the light emitting material may be one kind or two kinds or more. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.

  Further, the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.

  Although the thickness of the light emitting layer is not particularly limited, it is usually preferably 2 nm to 500 nm, more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm from the viewpoint of external quantum efficiency. More preferably.

In the organic electroluminescent element of the present invention, it is preferable that the light emitting layer contains a compound represented by the general formula (1), and the host material of the light emitting layer is represented by the general formula (1). It is a more preferable embodiment to use a compound. Here, in this specification, the host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and is a compound that itself does not substantially emit light. Here, “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
Hereinafter, as the material of the light emitting layer, the host material other than the light emitting material and the compound represented by the general formula (1) will be described in order. In addition, the compound represented by the said General formula (1) may be used other than the said light emitting layer in the organic electroluminescent element of this invention.

(Luminescent material)
As the light emitting material in the present invention, any of phosphorescent light emitting materials, fluorescent light emitting materials and the like can be used.
The light emitting layer in the present invention can contain two or more kinds of light emitting materials in order to improve the color purity and widen the light emission wavelength region. At least one of the light emitting materials is preferably a phosphorescent light emitting material.
In the present invention, in addition to at least one phosphorescent light-emitting material contained in the light-emitting layer, a fluorescent light-emitting material or a phosphorescent light-emitting material different from the phosphorescent light-emitting material contained in the light-emitting layer can be used as the light-emitting material.
Details of these fluorescent light-emitting materials and phosphorescent light-emitting materials are described in, for example, paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph numbers [0088] to [0090] of JP-A-2007-266458. The matters described in these publications can be applied to the present invention.

  Examples of phosphorescent light-emitting materials that can be used in the present invention include US Pat. / 19373A2, JP 2001-247859, JP 2002-302671, JP 2002-117978, JP 2003-133074, JP 2002-235076, JP 2003-123982, JP 2002-170684, EP 12112757, JP 2002/27 -226495, JP 2002-234894, JP 2001-247859, JP 2001-298470, JP 2002-17367. , JP2002-203678, JP2002-203679, JP2004-357799, JP2006-256999, JP2007-19462, JP2007-84635, JP2007-96259, WO07 / 095118, WO10 / 111175. And phosphorescent compounds described in patent documents such as WO10 / 027583 and WO10 / 028151, among which iridium (Ir) complex, platinum (Pt) complex, Cu complex, Re complex, Examples thereof include phosphorescent metal complex compounds such as W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd complex, Dy complex, and Ce complex. Particularly preferred is an iridium (Ir) complex, a platinum (Pt) complex, or a Re complex. Among them, at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, or a metal-sulfur bond is used. An iridium (Ir) complex, a platinum (Pt) complex, or a Re complex is preferable. Furthermore, iridium (Ir) complex and platinum (Pt) complex are particularly preferable, and iridium (Ir) complex is most preferable from the viewpoint of luminous efficiency, driving durability, chromaticity and the like.

  As a phosphorescent material contained in the light emitting layer in the present invention, an iridium (Ir) complex represented by the following general formula (E-1) or platinum represented by the following general formula (C-1) It is preferable to use a (Pt) complex.

  The iridium (Ir) complex represented by the general formula (E-1) will be described.

In general formula (E-1), Z < ¹ > and Z < ² > represent a carbon atom or a nitrogen atom each independently.
A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom.
B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom.
(XY) represents a monoanionic bidentate ligand.
n _E1 represents an integer of ₁ to 3. When n _E1 is 2 or 3, there will be 2 or 3 ligands containing Z ¹ , Z ² , A ₁ and B ₁ , They may be the same or different from each other.

n _E1 represents an integer of ₁ to 3, preferably 2 or 3, and more preferably 3.
Z ¹ and Z ² each independently represents a carbon atom or a nitrogen atom. Z ¹ and Z ² are preferably carbon atoms.

A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom. The 5- or 6-membered heterocycle containing A ₁ , Z ¹ and a nitrogen atom includes a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole Ring, thiadiazole ring and the like.
From the viewpoint of the stability of the complex, emission wavelength control and emission quantum yield, the 5- or 6-membered hetero ring formed by A ₁ , Z ¹ and a nitrogen atom is preferably a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole. A ring, more preferably a pyridine ring, an imidazole ring and a pyrazine ring, still more preferably a pyridine ring and an imidazole ring, and most preferably a pyridine ring.

The 5- or 6-membered heterocycle formed by A ₁ , Z ¹ and a nitrogen atom may have a substituent, and as a substituent on the carbon atom, the following substituent group A is on the nitrogen atom. The following substituent group B can be applied as the substituent. The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

<< Substituent group A >>
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl , 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 6 carbon atoms). 0, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, anthryl, etc.), amino group (preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms). Particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc.), an alkoxy group (preferably having 1 to 30 carbon atoms, and more. Preferably it is C1-C20, Most preferably, it is C1-C10, for example, a methoxy, an ethoxy, butoxy, 2-ethylhexyloxy etc. are mentioned), an aryloxy group (preferably C6-C30, More preferably, it has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms. And 1-naphthyloxy, 2-naphthyloxy, etc.), a heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms). For example, pyridyloxy, pyrazinyloxy, pyrimidinyloxy, quinolyloxy, etc.), an acyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, Acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, Ethoxycarbonyl, etc.), aryloxycarbonyl group (preferably carbon The number is 7 to 30, more preferably 7 to 20, and particularly preferably 7 to 12, and examples thereof include phenyloxycarbonyl. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as acetoxy and benzoyloxy), an acylamino group (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino, and the like, and an alkoxycarbonylamino group (preferably having 2-2 carbon atoms). 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino, etc.), aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino). ), A sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl Sulfamoyl, etc.), a carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, Phenylcarbamoyl etc.), alkylthio group ( Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methylthio, ethylthio and the like, and an arylthio group (preferably 6 to 30 carbon atoms). , More preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 to carbon atoms). 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, and a sulfonyl group (preferably having a carbon number). 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl). Rufinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl. ), A ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid. An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenylphosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group ( Heteroaryl group is also included, Preferably it is C1-C30, More preferably, it is C1-C12. Is, for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, And isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group and the like. Silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl). A silyloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, triphenylsilyloxy, etc.), phosphoryl group (for example, A diphenylphosphoryl group, a dimethylphosphoryl group, etc.). These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

<< Substituent group B >>
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl , 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 6 carbon atoms). 0, particularly preferably 6 to 12 carbon atoms, including phenyl, p-methylphenyl, naphthyl, anthryl, etc.), cyano group, heterocyclic group (including heteroaryl groups, preferably 1 carbon atom) To 30 and more preferably 1 to 12 carbon atoms, and the hetero atom is, for example, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, a selenium atom, or a tellurium atom, specifically, pyridyl or pyrazinyl. , Pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzimidazolyl, Nzothiazolyl, carbazolyl group, azepinyl group, silylyl group, etc.) These substituents may be further substituted, and examples of the further substituents include groups selected from the above-mentioned substituent group B. . Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above.

  The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, a heteroaryl group and the like are selected. In the case of increasing the wavelength, an electron withdrawing group is preferable, and for example, a cyano group, a perfluoroalkyl group, or the like is selected.

The substituent on nitrogen is preferably an alkyl group, an aryl group, or a heteroaryl group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.

B ₁ represents a 5- or 6-membered ring containing Z ² and a carbon atom. Examples of the 5- or 6-membered ring formed by B ₁ , Z ² and a carbon atom include a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, Examples include a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, and a furan ring.
From the viewpoint of the stability of the complex, emission wavelength control and emission quantum yield, the benzene ring, pyridine ring, pyrazine ring, imidazole ring, pyrazole is preferable as the 5- or 6-membered ring formed by B ₁ , Z ² and carbon atom. A ring and a thiophene ring, more preferably a benzene ring, a pyridine ring and a pyrazole ring, and still more preferably a benzene ring and a pyridine ring.

The 5- or 6-membered ring formed of B ₁ , Z ² and a carbon atom may have a substituent, and the substituent group A is a substituent on a nitrogen atom as a substituent on the carbon atom. As the above, the substituent group B can be applied. The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

  The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, A heteroaryl group or the like is selected. In order to shorten the wavelength, an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group, and the like are selected.

The substituent on nitrogen is preferably an alkyl group, an aryl group, or a heteroaryl group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex. The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.
The 5- or 6-membered heterocyclic substituent formed by A ₁ , Z ¹ and a nitrogen atom is linked to the 5- or 6-membered substituent formed by B ₁ , Z ² and a carbon atom. Then, the same condensed ring as described above may be formed.

Examples of the ligand represented by (XY) include various known ligands used in conventionally known metal complexes. For example, “Photochemistry and Photophysics of Coordination Compounds” Springer-Verlag H. Published by Yersin, 1987, “Organometallic Chemistry-Fundamentals and Applications-” Liu Huabosha, Akio Yamamoto, published by 1982, etc. (for example, halogen ligands (preferably chlorine ligands), Nitrogen heteroaryl ligands (for example, bipyridyl, phenanthroline, etc.), diketone ligands (for example, acetylacetone, etc.) are mentioned.
As the ligand represented by (X—Y), the following general formulas (l-1) to (l-13) are preferable, but the present invention is not limited thereto.

  * Represents a coordination position to iridium (Ir) in the general formula (E-1). Rx, Ry and Rz each independently represents a hydrogen atom or a substituent. G represents C—R or a nitrogen atom. R represents a hydrogen atom or a substituent.

  When Rx, Ry, and Rz represent a substituent, examples of the substituent include a substituent selected from the substituent group A. Preferably, Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, A fluorine atom and an optionally substituted phenyl group are most preferred, and a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group are most preferred. Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an optionally substituted phenyl group. And most preferably a hydrogen atom or a methyl group. Since these ligands are considered not to be sites where electrons are transported in the device or where electrons are concentrated by excitation, Rx, Ry, and Rz may be any chemically stable substituent, and the effects of the present invention can be achieved. Also has no effect.

R ^l1 to R ^l7 in the general formula (I-13) is preferably represents a substituent selected from substituent group A, may further have a substituent A.

  G represents C—R or a nitrogen atom. When R represents a substituent, examples of the substituent include a substituent selected from the substituent group A.

When R ^{11 to} R ^I7 and G represent C—R, any two of them may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl , Aryl or heteroaryl, and the fused 4- to 7-membered ring may further have a substituent.

The preferred range of R ^{11 to} R ^{17 is the same as} the preferred range of R ^{T1 to} R ^T7 in general formula (E-3) described later.

  G is preferably C—R, and R is preferably a hydrogen atom or an aryl group, more preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms (for example, a phenyl group, a tolyl group, A naphthyl group and the like, particularly preferably a hydrogen atom and a phenyl group.

  (XY) is more preferably (l-1), (l-4), (l-13), and particularly preferably (l-1), (l-13). Complexes having these ligands can be synthesized in the same manner as in known synthesis examples by using corresponding ligand precursors. For example, it can be synthesized in the same manner as described in International Publication 2009-073245, page 46.

  A preferred embodiment of the iridium (Ir) complex represented by the general formula (E-1) is an iridium (Ir) complex represented by the general formula (E-2).

In formula (E-2), A ^{E1 to} A ^E8 each independently represent a nitrogen atom or C—R ^E.
R ^E represents a hydrogen atom or a substituent.
(XY) represents a monoanionic bidentate ligand.
n _E2 represents an integer of 1 to 3.

A ^{E1 to} A ^E8 each independently represent a nitrogen atom or C—R ^E. R ^E represents a hydrogen atom or a substituent, and R ^E may be connected to each other to form a ring. Examples of the ring formed include the same condensed rings described in the general formula (E-1). As the substituent represented by R ^E , those exemplified as the substituent group A can be applied.
A ^E1 is preferably a to A ^E4 is C-R ^E, if A ^E1 to A ^E4 is C-R ^E, preferably a hydrogen atom R ^E of A ^E3, alkyl group, aryl group, amino group, An alkoxy group, an aryloxy group, a fluorine atom, or a cyano group, more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, and particularly preferably a hydrogen atom or a fluorine atom. R ^E in A ^E1 , A ^E2 and A ^E4 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, or a cyano group, more preferably a hydrogen atom, An alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, particularly preferably a hydrogen atom.

A ^{E5 to} A ^E8 are preferably C-R ^E , and when A ^{E5 to} A ^E8 are C-R ^E , R ^E is preferably a hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, heteroaryl Group, dialkylamino group, diarylamino group, alkyloxy group, cyano group, or fluorine atom, more preferably a hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, dialkylamino group, cyano group, or fluorine atom. And more preferably a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure. When the emission wavelength is shifted to the short wavelength side, A ^E6 is preferably a nitrogen atom.
(X-Y), and n _E2 of the general formula in (E1) (X-Y) , and has the same meaning as n _E1 preferable ranges are also the same.

  A more preferable form of the compound represented by the general formula (E-2) is a compound represented by the following general formula (E-3).

In the general formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, perfluoroalkyl group, trifluorovinyl _{group, -CO 2 R, -C (O} ) R, -NR 2, -NO 2, -OR, halogen atom, an aryl group or a heteroaryl group, a substituent You may have. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
A represents CR ′ or a nitrogen atom, and R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO ₂ R, —C (O ) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
R ^{T1 to} R ^T7 and R ′ may be combined with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl. The condensed 4- to 7-membered ring may further have a substituent. Of these, the case where R ^T1 and R ^T7 , or R ^T5 and R ^T6 are condensed to form a benzene ring is preferred, and the case where R ^T5 and R ^T6 are condensed to form a benzene ring is particularly preferred.
(X—Y) represents a monoanionic bidentate ligand. n _E3 represents an integer of 1 to 3.

The alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent A. The alkyl group represented by R ^{T1 to} R ^T7 and R ′ is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as methyl Group, ethyl group, i-propyl group, cyclohexyl group, t-butyl group and the like, and methyl group is particularly preferable.
The cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent A. The cycloalkyl group represented by R ^{T1 to} R ^T7 and R ′ is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total. A cyclopentyl group, a cyclohexyl group, etc. are mentioned.
The alkenyl group represented by R ^{T1 to} R ^T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, vinyl, allyl, Examples include 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, and 3-pentenyl.
The alkynyl group represented by R ^{T1 to} R ^T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include ethynyl and propargyl. , 1-propynyl, 3-pentynyl and the like.

Examples of the perfluoroalkyl group represented by R ^{T1 to} R ^T7 and R ′ include those in which all the hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.

Preferred examples of the aryl group represented by R ^{T1 to} R ^T7 and R ′ include a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, and a naphthyl group. A phenyl group is particularly preferred.

The heteroaryl group represented by R ^{T1 to} R ^T7 and R ′ is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted heteroaryl group. Groups such as pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, furyl, benzofuryl , Thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group, benzisothiazolyl group, thiadiazolyl group, isoxazolyl group Benz Sookisazoriru group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, a thiazolinyl group, a sulfolanyl group, a carbazolyl group, a dibenzofuryl group, dibenzothienyl group, such as 7 pyrido-indolyl group. Preferred examples include pyridyl group, pyrimidinyl group, imidazolyl group, and thienyl group, and more preferred are pyridyl group and pyrimidinyl group.

R ^{T1 to} R ^T7 and R ′ are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group or a heteroaryl group, more preferably A hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, and an aryl group are preferable, and a hydrogen atom, an alkyl group, and an aryl group are more preferable.

Any one of R ^{T1 to} R ^T7 and R ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl; The condensed 4- to 7-membered ring may further have a substituent. The definition and preferred range of cycloalkyl, aryl, and heteroaryl formed are the same as the cycloalkyl group, aryl group, and heteroaryl group defined by R ^{T1 to} R ^T7 and R ′.
Further, it is particularly preferable that A represents CR ′, and among R ^{T1 to} R ^T7 and R ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms, and R ^{T1 to} R ^T7 , And R ′ are particularly preferably 0 to 2 alkyl groups and the rest are all hydrogen atoms. Among R ^{T1 to} R ^T7 and R ′, 0 to 2 are methyl groups and the rest are all hydrogen atoms. Most preferred is an atom.

n _E3 is preferably 2 or 3. The type of ligand in the complex is preferably composed of 1 to 2 types, and more preferably 1 type. When introducing a reactive group into the complex molecule, it is also preferred that the ligand consists of two types from the viewpoint of ease of synthesis.
(XY) is synonymous with (XY) in general formula (E-1), and its preferable range is also the same.

  One of the preferable forms of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-4).

R ^{T1 to} R ^T4 , A, (XY) and n _E4 in the general formula (E-4) are R ^{T1 to} R ^T4 , A, (XY) and n _{E3 in the} general formula (E-3). The preferred range is also the same. R ₁ ′ to R ₅ ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R. , —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any _{one of} R ₁ ′ to R ₅ ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The condensed 4- to 7-membered ring may further have a substituent.
Moreover, the preferable range in R < ₁ >'-R< ₅ >' is the same as R ^{< T1} > -R <^T7> , R 'in general formula (E-3). Further, it is particularly preferable that A represents CR ′, and among R ^{T1 to} R ^T4 , R ′, and R ₁ ′ to R ₅ ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms. , R ^{T1 to} R ^T4 , R ′, and R ₁ ′ to R ₅ ′, 0 to 2 are more preferably alkyl groups and the rest are all hydrogen atoms.

  Another preferable form of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-5).

R ^{T2 to} R ^T6 , A, (XY) and n _E5 in the general formula (E-5) are R ^{T2 to} R ^T6 , A, (XY) and n _{E3 in the} general formula (E-3). The preferred range is also the same. R ₆ ′ to R ₈ ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R. , —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
R ^T5 , R ^T6 , R ₆ ′ to R ₈ ′ may be combined with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or It is heteroaryl, and the condensed 4- to 7-membered ring may further have a substituent.
Moreover, the preferable range in R < ₆ >'-R< ₈ >' is the same as R ^{< T1} > -R <^T7> , R 'in general formula (E-3). Further, it is particularly preferable that A represents CR ′, and among R ^{T2 to} R ^T6 , R ′, and R ₆ ′ to R ₈ ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms. , R ^{T2 to} R ^T6 , R ′, and R ₆ ′ to R ₈ ′, 0 to 2 are alkyl groups, and the rest are all preferably hydrogen atoms.

  When the phosphorescent material represented by the general formula (E-4) or (E-5) is used, the compound represented by the general formula (1) is preferably contained in the light emitting layer or the hole blocking layer. More preferably, it is contained in the light emitting layer.

  Another preferable embodiment of the compound represented by the general formula (E-1) is a case represented by the following general formula (E-6).

In General Formula (E-6), R _{1a to} R _1k each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, —CO _2. R, —C (O) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any two of R _{1a to} R _1k may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The -7 membered ring may further have a substituent.
(X—Y) represents a monoanionic bidentate ligand.
n _E6 represents an integer of 1 to 3.

In the general formula (E-6), preferred ranges of R _{1a to} R _1k are the same as those in R ^{T1 to} R ^T7 and R ′ in the general formula (E-3). In addition, it is particularly preferable that 0 to 2 of R _{1a to} R _1k are alkyl groups or phenyl groups and the rest are all hydrogen atoms, and 0 to 2 of R _{1a to} R _1k are alkyl groups and the rest are all hydrogen. More preferably, it is an atom.
The case where R _1j and R _1k are linked to form a single bond is particularly preferable.
The preferred range of (XY) and n _E6 is the same as (XY) and n _E3 in general formula (E-3).

  A more preferable form of the compound represented by the general formula (E-6) is a case represented by the following general formula (E-7).

In General Formula (E-7), R _{1a to} R _1i each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, —CO _2. R, —C (O) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any two of R _{1a to} R _1k may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is a cycloalkyl group, an aryl group, or a heteroaryl group; The condensed 4- to 7-membered ring may further have a substituent.
(X—Y) represents a monoanionic bidentate ligand.
n _E7 represents an integer of 1 to 3.

In the formula (E-7), definition and preferable ranges of R _1a to R _1i are the same as R _1a to R _1i in the formula (E-6). Further, among R _{1a to} R _1i , it is particularly preferable that 0 to 2 are alkyl groups or aryl groups, and the rest are all hydrogen atoms. The definitions and preferred ranges of (X—Y) and n _E7 are the same as (X—Y) and n _E3 in general formula (E-3).

  When the phosphorescent material represented by the general formula (E-6) or (E-7) is used, the compound represented by the general formula (1) is preferably contained in the light emitting layer or the hole blocking layer. .

One of the preferable forms of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-8).

R ^{T1 to} R ^T7 in the general formula (E-8) have the same ^{meanings as those} in the general formula (E-3), and preferred ranges thereof are also the same. R ^{11 to} R ¹⁷ and G have the same ^{meanings as} those in the ligand ( ^1-13 ), and preferred ranges thereof are also the same. R ′ represents a hydrogen atom or a substituent selected from substituent group A. R ′ is preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluorine atom, an aryl group, or a heteroaryl group, more preferably a hydrogen atom, an alkyl group, A fluorine atom or an aryl group, more preferably a hydrogen atom. n _E8 represents an integer of 1 to 3, and is preferably 2 or 1.

One of the preferable forms of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-9).

R ^T1 and R ^{T3 to} R ^T7 in the general formula (E-9) have the same ^{meanings as those} in the general formula (E-3), and preferred ranges thereof are also the same. R ^{11 to} R ¹⁷ and G have the same ^{meanings as} those in the ligand ( ^1-13 ), and preferred ranges thereof are also the same. R ′ represents a hydrogen atom or a substituent selected from substituent group A. R ′ is preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluorine atom, an aryl group, or a heteroaryl group, more preferably a hydrogen atom, an alkyl group, A fluorine atom or an aryl group, more preferably a hydrogen atom. n _E9 represents an integer of 1 to 3, and is preferably 2 or 1. X represents an oxygen atom or a sulfur atom.

  Although the preferable specific example of a compound represented by general formula (E-1) is enumerated below, it is not limited to the following.

  The compound illustrated as a compound represented by the said general formula (E-1) is compoundable by the method as described in Unexamined-Japanese-Patent No. 2009-99783, the various method as described in US Patent 7279232, etc. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

  Although it is preferable that the compound represented by general formula (E-1) is contained in a light emitting layer, the use is not limited and may further be contained in any layer in the organic layer. .

  The compound represented by the general formula (E-1) in the light emitting layer is contained in an amount of 0.1% by mass to 50% by mass with respect to the total compound mass generally forming the light emitting layer in the light emitting layer. From the viewpoint of durability and external quantum efficiency, it is preferably contained in an amount of 1% by mass to 50% by mass, more preferably 2% by mass to 40% by mass.

  A compound represented by any one of the general formulas (1) to (3) and (6) and a compound represented by any one of the general formulas (E-1) to (E-9) are combined in the light emitting layer. It is particularly preferable in the present invention to use them.

  The platinum (Pt) complex that can be used as the phosphorescent material is preferably a platinum (Pt) complex represented by the following general formula (C-1).

(In the formula, Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand coordinated to platinum (Pt). L ¹ , L ² and L ³ are each independently a single bond or a divalent group. Represents a linking group.)

General formula (C-1) is demonstrated. Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand coordinated to platinum (Pt). At this time, the bond between Q ¹ , Q ² , Q ³ and Q ⁴ and platinum (Pt) may be any of a covalent bond, an ionic bond, a coordinate bond, and the like. As an atom couple | bonded with platinum (Pt) in Q < ¹ >, Q < ² >, Q < ³ > and Q < ⁴ >, a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, Q < ¹ >, Q < ² >, Q < ³ > Of the atoms bonded to platinum (Pt) in Q ⁴ , at least one is preferably a carbon atom, more preferably two are carbon atoms, two are carbon atoms, and two are nitrogen atoms. Is particularly preferred.
Q ¹ , Q ² , Q ^3, and Q ⁴ bonded to platinum (Pt) by a carbon atom may be an anionic ligand or a neutral ligand, and the anionic ligand is a vinyl group. Ligand, aromatic hydrocarbon ring ligand (eg benzene ligand, naphthalene ligand, anthracene ligand, phenanthrene ligand, etc.), heterocyclic ligand (eg furan ligand, thiophene coordination) Pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole coordination Child, a triazole ligand, and a condensed ring containing them (for example, quinoline ligand, benzothiazole ligand, etc.). A carbene ligand is mentioned as a neutral ligand.

The groups represented by Q ¹ , Q ² , Q ³ and Q ⁴ may have a substituent, and as the substituent, those exemplified as the substituent group A can be appropriately applied. Moreover, substituents may be connected to each other (when Q ³ and Q ⁴ are connected, a platinum (Pt) complex of a cyclic tetradentate ligand is formed).

The group represented by Q ¹ , Q ² , Q ³ and Q ⁴ is preferably an aromatic hydrocarbon ring ligand bonded to platinum (Pt) by a carbon atom, and an aromatic bonded to platinum (Pt) by a carbon atom. Heterocyclic heterocyclic ligands, nitrogen-containing aromatic heterocyclic ligands bonded to platinum (Pt) with nitrogen atoms, acyloxy ligands, alkyloxy ligands, aryloxy ligands, heteroaryloxy ligands A silyloxy ligand, more preferably an aromatic hydrocarbon ring ligand bonded to platinum (Pt) at a carbon atom, an aromatic heterocyclic ligand bonded to platinum (Pt) at a carbon atom, nitrogen Nitrogen-containing aromatic heterocyclic ligands, acyloxy ligands, and aryloxy ligands bonded to platinum (Pt) with atoms, more preferably aromatic hydrocarbon rings bonded to platinum (Pt) with carbon atoms Ligand, carbon atom platinum (Pt) An aromatic heterocyclic ligand bonded to the nitrogen atom, a nitrogen-containing aromatic heterocyclic ligand bonded to platinum (Pt) with a nitrogen atom, and an acyloxy ligand.

L ¹ , L ² and L ³ represent a single bond or a divalent linking group. Divalent linking groups represented by L ¹ , L ² and L ³ include alkylene groups (methylene, ethylene, propylene, etc.), arylene groups (phenylene, naphthalenediyl), heteroarylene groups (pyridinediyl, thiophenediyl, etc.) ), Imino group (—NR—) (such as phenylimino group), oxy group (—O—), thio group (—S—), phosphinidene group (—PR—) (such as phenylphosphinidene group), silylene group (-SiRR'-) (dimethylsilylene group, diphenylsilylene group, etc.), or a combination of these. Here, R and R ′ each independently include an alkyl group, an aryl group, and the like. These linking groups may further have a substituent.
From the viewpoint of the stability of the complex and the light emission quantum yield, L ¹ , L ² and L ³ are preferably single bonds, alkylene groups, arylene groups, heteroarylene groups, imino groups, oxy groups, thio groups, and silylene groups. More preferably a single bond, an alkylene group, an arylene group or an imino group, still more preferably a single bond, an alkylene group or an arylene group, still more preferably a single bond, a methylene group or a phenylene group, still more preferably. Single bond, disubstituted methylene group, more preferably single bond, dimethylmethylene group, diethylmethylene group, diisobutylmethylene group, dibenzylmethylene group, ethylmethylmethylene group, methylpropylmethylene group, isobutylmethylmethylene group, diphenyl Methylene group, methylphenylmethylene group, cyclohexanediyl group, cyclope An tandiyl group, a fluorenediyl group, and a fluoromethylmethylene group.
L ¹ is particularly preferably a dimethylmethylene group, a diphenylmethylene group, or a cyclohexanediyl group, and most preferably a dimethylmethylene group.
L ² and L ³ are most preferably a single bond.

Of the platinum (Pt) complexes represented by the general formula (C-1), a platinum (Pt) complex represented by the following general formula (C-2) is more preferable.

(In the formula, L ²¹ represents a single bond or a divalent linking group. A ²¹ and A ²² each independently represents a carbon atom or a nitrogen atom. Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic heterocyclic ring. Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic heterocycle.

General formula (C-2) is demonstrated. L ²¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

A ²¹ and A ²² each independently represent a carbon atom or a nitrogen atom. Of A ^21, A ^22, Preferably, at least one is a carbon atom, it A ^21, A ²² are both carbon atoms are preferred from the standpoint of emission quantum yield stability aspects and complexes of the complex .

Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic heterocycle. Examples of the nitrogen-containing aromatic heterocycle represented by Z ²¹ and Z ²² include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, Examples include thiadiazole rings. From the viewpoints of complex stability, emission wavelength control and emission quantum yield, the ring represented by Z ²¹ and Z ²² is preferably a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole ring, more preferably a pyridine ring. , An imidazole ring and a pyrazole ring, more preferably a pyridine ring and a pyrazole ring, and particularly preferably a pyridine ring.

Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic heterocycle. Examples of the nitrogen-containing aromatic heterocycle represented by Z ²³ and Z ²⁴ include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadi Examples include an azole ring, a thiadiazole ring, a thiophene ring, and a furan ring. From the viewpoint of stability of the complex, emission wavelength control and emission quantum yield, the ring represented by Z ²³ and Z ²⁴ is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, or a thiophene ring, More preferred are a benzene ring, a pyridine ring and a pyrazole ring, and still more preferred are a benzene ring and a pyridine ring.

  Of the platinum (Pt) complexes represented by the general formula (C-2), one of more preferable embodiments is a platinum (Pt) complex represented by the following general formula (C-4).

(In the general formula (C-4), A ^{401 to} A ⁴¹⁴ each independently represents C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁴¹ represents a single bond or a divalent linking group. To express.)

General formula (C-4) is demonstrated.
A ^{401 to} A ⁴¹⁴ each independently represents C—R or a nitrogen atom. R represents a hydrogen atom or a substituent.
As the substituent represented by R, those exemplified as the substituent group A can be applied.
A ^{401 to} A ⁴⁰⁶ are preferably C—R, and Rs may be connected to each other to form a ring. When A ^{401 to} A ⁴⁰⁶ are C—R, R in A ⁴⁰² and A ⁴⁰⁵ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, or a cyano group. More preferably a hydrogen atom, an amino group, an alkoxy group, an aryloxy group or a fluorine atom, and particularly preferably a hydrogen atom or a fluorine atom. R in A ⁴⁰¹ , A ⁴⁰³ , A ⁴⁰⁴ and A ⁴⁰⁶ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably a hydrogen atom or amino Group, an alkoxy group, an aryloxy group and a fluorine atom, and particularly preferably a hydrogen atom.
L ⁴¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

As A ^{407 to} A ⁴¹⁴ , in each of A ^{407 to} A ⁴¹⁰ and A ^{411 to} A ⁴¹⁴ , the number of N (nitrogen atoms) is preferably 0 to 2, and more preferably 0 to 1. When shifting the emission wavelength to the short wavelength side, either A ⁴⁰⁸ or A ⁴¹² is preferably a nitrogen atom, and more preferably both A ⁴⁰⁸ and A ⁴¹² are nitrogen atoms.

  Of the platinum (Pt) complexes represented by the general formula (C-2), one of more preferred embodiments is a platinum (Pt) complex represented by the following general formula (C-5).

(In the general formula (C-5), A ^{501 to} A ⁵¹² each independently represents C—R or a nitrogen atom, R represents a hydrogen atom or a substituent, and L ⁵¹ represents a single bond or a divalent linkage. Represents a group.)

General formula (C-5) is demonstrated. A ^{501 to} A ⁵⁰⁶ and L ⁵¹ have the same meanings as A ^{401 to} A ⁴⁰⁶ and L ⁴¹ in the general formula (C-4), and preferred ranges thereof are also the same.

A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² and each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied.

  Among the platinum (Pt) complexes represented by the general formula (C-1), another more preferable embodiment is a platinum (Pt) complex represented by the following general formula (C-6).

(In the formula, L ⁶¹ represents a single bond or a divalent linking group. A ⁶¹ independently represents a carbon atom or a nitrogen atom. Z ⁶¹ and Z ⁶² each independently represent a nitrogen-containing aromatic heterocycle. Z ⁶³ independently represents a benzene ring or an aromatic heterocycle, and Y is an anionic acyclic ligand bonded to platinum (Pt).

General formula (C-6) is demonstrated. L ⁶¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

A ⁶¹ represents a carbon atom or a nitrogen atom. In view of the stability of the complex and the light emission quantum yield of the complex, A ⁶¹ is preferably a carbon atom.

Z ⁶¹ and Z ⁶² are synonymous with Z ²¹ and Z ²² in the general formula (C-2), respectively, and preferred ranges thereof are also the same. Z ⁶³ has the same meaning as Z ²³ in formula (C-2), and the preferred range is also the same.

Y is an anionic acyclic ligand that binds to platinum (Pt). An acyclic ligand is one in which atoms bonded to platinum (Pt) do not form a ring in the state of a ligand. As an atom couple | bonded with platinum (Pt) in Y, a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom are preferable, a nitrogen atom and an oxygen atom are more preferable, and an oxygen atom is the most preferable.
A vinyl ligand is mentioned as Y couple | bonded with platinum (Pt) by a carbon atom. Examples of Y bonded to platinum (Pt) with a nitrogen atom include an amino ligand and an imino ligand. Examples of Y bonded to platinum (Pt) with an oxygen atom include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, a carboxyl ligand, and a phosphate group. Examples thereof include ligands and sulfonic acid ligands. Examples of Y bonded to platinum (Pt) with a sulfur atom include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, and thiocarboxylic acid ligands.
The ligand represented by Y may have a substituent, and those exemplified as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other.

  The ligand represented by Y is preferably a ligand bonded to platinum (Pt) with an oxygen atom, and more preferably an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy A ligand and a silyloxy ligand are preferable, and an acyloxy ligand is more preferable.

  Of the platinum (Pt) complexes represented by the general formula (C-6), one of more preferable embodiments is a platinum (Pt) complex represented by the following general formula (C-7).

(In the formula, A ^{701 to} A ⁷¹⁰ each independently represents C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁷¹ represents a single bond or a divalent linking group. Y represents (It is an anionic acyclic ligand that binds to platinum (Pt).)

General formula (C-7) is demonstrated. L ⁷¹ has the same meaning as L ^{61 in} formula (C-6), and the preferred range is also the same. A ^{701 to} A ⁷¹⁰ have the same meanings as A ^{401 to} A ⁴¹⁰ in formula (C-4), and the preferred ranges are also the same. Y has the same meaning as Y in formula (C-6), and the preferred range is also the same.

  Specific examples of the platinum (Pt) complex represented by the general formula (C-1) include [0143] to [0152], [0157] to [0158], and [0162] to JP-A-2005-310733. Compounds described in [0168], compounds described in [0065] to [0083] of JP 2006-256999 A, compounds described in [0065] to [0090] of JP 2006-93542 A, JP The compounds described in [0063] to [0071] of 2007-73491, the compounds described in [0079] to [0083] of JP 2007-324309, and [0065] to [0065] of JP 2006-93542 A Compound described in [0090], compound described in [0055] to [0071] of JP-A-2007-96255, JP-A-2006-313796 Include [0043] - [0046] of JP, other platinum (Pt) complex and the like to be exemplified below.

The platinum (Pt) complex compound represented by the general formula (C-1) is, for example, Journal of Organic Chemistry 53,786, (1988), G.A. R. Newkome et al. ), Page 789, method described in left column 53 to right column 7, line 790, method described in left column 18 to 38, method 790, method described in right column 19 to 30 and The combination, Chemische Berichte 113, 2749 (1980), H.C. Lexy et al.), Page 2752, lines 26-35, and the like.
For example, a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent, In the presence of a sulfoxide solvent, water, etc., or in the absence of a solvent, in the presence of a base (inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.) Or in the absence of a base, at room temperature or below, or by heating (in addition to normal heating, a method of heating with a microwave is also effective).

  The content of the compound represented by the general formula (C-1) in the light emitting layer of the organic electroluminescent element of the present invention is preferably 1 to 30% by mass, and 3 to 25% by mass in the light emitting layer. Is more preferable, and it is still more preferable that it is 5-20 mass%.

The type of the fluorescent material is not particularly limited. For example, benzoxazole, benzimidazole, benzothiazole, styrylbenzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin, pyran, perinone, oxa Diazole, aldazine, pyralidine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine, condensed polycyclic aromatic compounds (anthracene, phenanthrene, pyrene, perylene, fluoranthene, rubrene, chrysene) , Or pentacene), metal complexes of 8-quinolinol, various metal complexes typified by pyromethene complexes and rare earth complexes, polythiophene, polyphenylene, polyphenylene Polymeric compounds such as Nirenbiniren, organic silane, and may be derivatives of these.
Specific examples of the fluorescent material are shown below, but the present invention is not limited to these.

  The content of the fluorescent light emitting material in the light emitting layer of the organic electroluminescent element of the present invention is preferably 1 to 30% by mass, more preferably 1 to 20% by mass in the light emitting layer. More preferably.

In the present invention, from the viewpoint of preventing quenching with the compound represented by the general formula (1), the maximum emission wavelength of the light emitting material is preferably 400 to 700 nm, more preferably 500 to 700 nm. More preferably, it is -650nm, and it is most preferable that it is 520-550nm.
The maximum light emission wavelength of the phosphorescent material represented by the general formula (E-3) is in the range of about 500 to 550 nm when a plurality of R ^{T1 to} R ^T7 and R ′ do not form a ring together, The maximum emission wavelength of the phosphorescent material represented by (E-4) or (E-5) is in the range of about 550 to 650 nm.

  The thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm, and more preferably 10 nm to 100 nm, from the viewpoint of external quantum efficiency. More preferably.

The light emitting layer in the organic electroluminescent element of the present invention may be composed only of a light emitting material, or may be a mixed layer of a host material and a light emitting material. The kind of the light emitting material may be one kind or two or more kinds. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may contain a material that does not have charge transporting properties and does not emit light.
Further, the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.

(Host material)
The host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and itself is a compound that does not substantially emit light. Here, “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
As the host material, a compound represented by the general formula (1) can be used.

Examples of other host materials that can be used in the organic electroluminescence device of the present invention include the following compounds.
Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, aryl Amine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, porphyrin-based compound, condensed aromatic hydrocarbon compound (anthracene, pyrene, fluorene, naphthalene, phenanthrene) , Triphenylene, etc.), polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiopheneol , Conductive polymer oligomers such as polythiophene, organic silane, carbon film, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone Thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanines, metal complexes of 8-quinolinol derivatives and metal phthalocyanines, Examples thereof include various metal complexes represented by metal complexes having benzoxazole or benzothiazol as a ligand, and derivatives thereof (which may have a substituent or a condensed ring).
Of these, carbazole, dibenzothiophene, dibenzofuran, arylamine, fused aromatic hydrocarbon compounds, and metal complexes are particularly preferable.

  The host material that can be used in combination in the light emitting layer of the organic electroluminescent device of the present invention may be a hole transporting host material or an electron transporting host material.

In the light emitting layer, the triplet lowest excitation energy (T ₁ energy) in the film state of the host material is preferably higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable T ₁ is greater 0.1eV higher than the T ₁ of the phosphorescent material of the host material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
T ₁ of the a film state of the host material is a large T ₁ is obtained from the phosphorescent material to the host material for thereby quench T ₁ is less than the light emission of the phosphorescent material. Even if the T _{1 of} the host material is larger than the phosphorescent light emitting material, if the difference in T ₁ between the two is small, the reverse energy transfer from the phosphorescent light emitting material to the host material occurs in part, resulting in a decrease in efficiency and durability. Cause. Therefore, there is a demand for a host material having a sufficiently large T ₁ and high chemical stability and carrier injection / transport properties.

  In addition, the content of the host compound in the light emitting layer in the organic electroluminescent device of the present invention is not particularly limited, but is 15 mass with respect to the total compound mass forming the light emitting layer from the viewpoint of light emission efficiency and driving voltage. % Or more and 95% by mass or less is preferable. When the light emitting layer contains a plurality of types of host compounds including the compound represented by the general formula (1), the compound represented by the general formula (1) is 50% by mass or more and 99% by mass or less in all the host compounds. It is preferable.

(Other layers)
The organic electroluminescent element of the present invention may have other layers other than the light emitting layer.
Other organic layers other than the light emitting layer that the organic layer may have include a hole injection layer, a hole transport layer, a block layer (hole block layer, exciton block layer, etc.), an electron transport layer, and the like. Is mentioned. Examples of the specific layer configuration include the following, but the present invention is not limited to these configurations.
Anode / hole transport layer / light emitting layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / block layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode.
The organic electroluminescent element of the present invention preferably comprises (A) at least one organic layer preferably disposed between the anode and the light emitting layer. Examples of the organic layer (A) preferably disposed between the anode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron block layer from the anode side.
The organic electroluminescent element of the present invention preferably includes (B) at least one organic layer preferably disposed between the cathode and the light emitting layer. Examples of the organic layer (B) preferably disposed between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer from the cathode side.
Specifically, an example of a preferable embodiment of the organic electroluminescent element of the present invention is the embodiment described in FIG. In this embodiment, the light emitting layer 6, the hole blocking layer 7, and the electron transport layer 8 are laminated in this order.
Hereinafter, other layers other than the light emitting layer which may be included in the organic electroluminescent element of the present invention will be described.

(A) Organic layer preferably disposed between the anode and the light emitting layer First, (A) the organic layer preferably disposed between the anode and the light emitting layer will be described.

(A-1) Hole injection layer, hole transport layer The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
Regarding the hole injection layer and the hole transport layer, the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention.

The hole injection layer preferably contains an electron accepting dopant. By containing an electron-accepting dopant in the hole injection layer, hole injection properties are improved, driving voltage is reduced, and efficiency is improved. The electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the doped material and generate radical cations. For example, tetracyanoquinodimethane ( TCNQ), tetrafluorotetracyanoquinodimethane (F ₄ -TCNQ), molybdenum oxide and the like.

  The electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and 0.1% by mass to 40% by mass with respect to the total compound mass forming the hole injection layer. % Content is more preferable, and 0.2% by mass to 30% by mass is more preferable.

(A-2) Electron Blocking Layer The electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side. In the present invention, an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
As an example of the organic compound constituting the electron blocking layer, for example, those mentioned as the hole transport material described above can be applied.
The thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, and still more preferably 5 nm to 50 nm.
The electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
The material used for the electron blocking layer is preferably higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable T ₁ is greater than 0.1eV than T ₁ of the phosphorescent material in the film state of the material used for the electron blocking layer, it is more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.

(B) Organic layer preferably disposed between the cathode and the light emitting layer Next, the (B) organic layer preferably disposed between the cathode and the light emitting layer will be described.

(B-1) Electron injection layer and electron transport layer The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. The electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
As the electron transport material, the compound represented by the general formula (1) can be used. Other electron transport materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, benzimidazole derivatives, imidazopyridine derivatives. , Fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic tetracarboxylic anhydrides such as naphthalene and perylene, Metal complexes of phthalocyanine derivatives and 8-quinolinol derivatives, metal phthalocyanines, benzoxazoles and benzothiazoles as ligands Various metal complexes typified by metal complexes, organosilane derivatives typified by siloles, condensed hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, triphenylene, pyrene, etc., are preferred, pyridine derivatives, benzimidazole derivatives , An imidazopyridine derivative, a metal complex, or a condensed ring hydrocarbon compound is more preferable.

The thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
The thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm. In addition, the thickness of the electron injection layer is preferably 0.1 nm to 200 nm, more preferably 0.2 nm to 100 nm, and still more preferably 0.5 nm to 50 nm.
The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

  The electron injection layer preferably contains an electron donating dopant. By including an electron donating dopant in the electron injection layer, the electron injection property is improved, the driving voltage is lowered, and the efficiency is improved. The electron donating dopant may be any organic material or inorganic material as long as it can give electrons to the doped material and generate radical anions. For example, tetrathiafulvalene (TTF) , Dithiimidazole compounds such as tetrathianaphthacene (TTT) and bis- [1,3 diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, cesium and the like.

  The electron donating dopant in the electron injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and 0.1% by mass to 40% by mass, based on the total mass of the compound forming the electron injection layer. It is more preferable that 0.5% by mass to 30% by mass is contained.

(B-2) Hole blocking layer The hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side. In the present invention, a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
The T ₁ energy in the film state of the organic compound constituting the hole blocking layer is higher than the T ₁ energy of the light emitting material in order to prevent energy transfer of excitons generated in the light emitting layer and not to reduce the light emission efficiency. It is preferable.
As an example of the organic compound constituting the hole blocking layer, the compound represented by the general formula (1) can be used.
Examples of other organic compounds constituting the hole blocking layer other than the compound represented by the general formula (1) include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate ( Aluminum complexes such as aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as Balq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( Phenanthroline derivatives such as 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)) and the like.
The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, and still more preferably 5 nm to 50 nm.
The hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.
The material used for the hole blocking layer is preferably higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability. Holes T ₁ of the at film state of the material used in the blocking layer is preferably greater 0.1eV higher than the T ₁ of the phosphorescent material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV greater .

(B-3) Material particularly preferably used for the organic layer preferably disposed between the cathode and the light emitting layer The organic electroluminescent element of the present invention is preferably disposed between the (B) cathode and the light emitting layer. As a material particularly preferably used for the material of the organic layer, a compound represented by the general formula (1), a compound represented by the following general formula (P-1), and a compound represented by the following general formula (O-1) Can be mentioned.
Hereinafter, the compound represented by the general formula (O-1) and the compound represented by the general formula (P-1) will be described.

  The organic electroluminescent device of the present invention preferably includes at least one organic layer between the light emitting layer and the cathode, and the organic layer contains at least one compound represented by the following general formula (O-1). It is preferable from the viewpoint of device efficiency and driving voltage. Below, general formula (O-1) is demonstrated.

In (formula (O1), R ^O1 represents an alkyl group, an aryl group, or .A ^O1 to A ^O4 representing the heteroaryl group each independently may .R ^A representing a C-R ^A or a nitrogen atom Represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different, L ^O1 represents a divalent to hexavalent linking group consisting of an aryl ring or a heteroaryl ring; N ^O1 represents an integer of 2 to 6.)

R ^O1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms), and these are the aforementioned substituents. It may have a substituent selected from group A. R ^O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. A preferable substituent when the aryl group of R ^O1 has a substituent includes an alkyl group, an aryl group or a cyano group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group. When the aryl group of R ^O1 has a plurality of substituents, the plurality of substituents may be bonded to each other to form a 5- or 6-membered ring. The aryl group of R ^O1 is preferably a phenyl group which may have a substituent selected from the substituent group A, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, More preferred is an unsubstituted phenyl group or 2-phenylphenyl group.

A ^{O1 to} A ^O4 each independently represent C—R ^A or a nitrogen atom. Of A ^{O1 to} A ^O4 , 0 to 2 are preferably nitrogen atoms, and 0 or 1 is more preferably a nitrogen atom. It is preferred that all of A ^{O1 to} A ^O4 are C—R ^A , or A ^O1 is a nitrogen atom and A ^{O2 to} A ^O4 are C—R ^A , A ^O1 is a nitrogen atom, and A ^O2 to More preferably, A ^O4 is C—R ^A , A ^O1 is a nitrogen atom, A ^{O2 to} A ^O4 are C—R ^A , and all R ^A are hydrogen atoms.

R ^A represents a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). It may have a substituent selected from the substituent group A. The plurality of R ^A may be the same or different. R ^A is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.

L ^O1 represents a divalent to hexavalent linking group composed of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms). L ^O1 is preferably an arylene group, heteroarylene group, aryltriyl group, or heteroaryltriyl group, more preferably a phenylene group, a biphenylene group, or a benzenetriyl group, still more preferably a biphenylene group, Or it is a benzenetriyl group. L ^O1 may have a substituent selected from the aforementioned substituent group A, and the alkyl group, aryl group, or cyano group is preferred as the substituent when it has a substituent. Specific examples of L ^O1 include the following.

n ^O1 represents an integer of 2 to 6, preferably an integer of 2 to 4, and more preferably 2 or 3. n ^O1 is most preferably 3 in terms of device efficiency, and most preferably 2 in terms of device durability.
The compound represented by the general formula (O-1) is more preferably a compound represented by the following general formula (O-2).

(In General Formula (O-2), R ^O1 represents an alkyl group, an aryl group, or a heteroaryl group. R ^{O2 to} R ^O4 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. A ^{O1 to} A ^O4 each independently represents C—R ^A or a nitrogen atom, R ^A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A are the same or different. May be.)

R ^O1 and A ^O1 to A ^O4, the general formula (O1) in the same meaning as R ^O1 and A ^O1 to A ^O4 of, also the same preferable ranges thereof.
R ^{02 to} R ⁰⁴ are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). These may have a substituent selected from the aforementioned substituent group A. R ^{02 to} R ⁰⁴ are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an aryl group, and most preferably a hydrogen atom.

  The compound represented by the general formula (O-1) has a glass transition temperature (Tg) of 100 ° C. from the viewpoint of stability at high temperature storage, stable operation against high temperature driving, and heat generation during driving. It is preferably ˜300 ° C., more preferably 120 ° C. to 300 ° C., still more preferably 120 ° C. to 300 ° C., and still more preferably 140 ° C. to 300 ° C.

  Specific examples of the compound represented by the general formula (O-1) are shown below, but the present invention is not limited thereto.

  The compound represented by the general formula (O-1) can be synthesized by the method described in JP-A No. 2001-335776. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.

In the organic electroluminescent device of the present invention, the compound represented by the general formula (O-1) is preferably contained in the organic layer between the light emitting layer and the cathode, but the layer on the cathode side adjacent to the light emitting layer. It is more preferable that it is contained.
It is preferable that 70-100 mass% is contained with respect to the total mass of the organic layer to add, and, as for the compound represented by general formula (O-1), it is more preferable that 85-100 mass% is contained.

  The organic electroluminescent element of the present invention preferably contains at least one organic layer between the light emitting layer and the cathode, and contains at least one compound represented by the following general formula (P) in the organic layer. Is preferable from the viewpoints of element efficiency and driving voltage. Below, general formula (P) is demonstrated.

(In General Formula (P), R ^P represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). And these may have a substituent selected from the aforementioned substituent group A. nP represents an integer of 1 to 10, and when there are a plurality of R ^P , they may be the same or different. At least one of R ^P is a substituent represented by the following general formulas (P-1) to (P-3).

(In the general formulas (P-1) to (P-3), R ^{P1 to} R ^P3 and R ′ ^{P1 to} R ′ ^P3 represent an alkyl group (preferably having 1 to 8 carbon atoms) and an aryl group (preferably having a carbon number). 6-30) or a heteroaryl group (preferably having 4 to 12 carbon atoms), which may have a substituent selected from the aforementioned substituent group A. n ^P1 and n ^P2 are 0 to 0, respectively. It represents an integer of 4, and when R ^{P1 to} R ^P3 and R ′ ^{P1 to} R ′ ^P3 are plural, they may be the same or different, and L ^{P1 to} L ^P3 are a single bond, an aryl ring or a heteroaryl ring. Represents one of divalent linking groups consisting of: * represents a bonding position with the anthracene ring of formula (P)

As R ^P , a preferable substituent other than the substituents represented by (P-1) to (P-3) is an aryl group, and more preferably one of a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group. And more preferably a naphthyl group.
R ^{P1 to} R ^P3 and R ′ ^{P1 to} R ′ ^P3 are preferably either an aryl group or a heteroaryl group, more preferably an aryl group, still more preferably a phenyl group, a biphenyl group, a terphenyl group, It is either a naphthyl group, most preferably a phenyl group.
L ^{P1 to} L ^P3 are preferably any of a single bond and a divalent linking group comprising an aryl ring, more preferably a single bond, phenylene, biphenylene, terphenylene or naphthylene, and even more preferably It is either a single bond, phenylene, or naphthylene.

  Although the specific example of a compound represented by general formula (P) is shown below, this invention is not limited to these.

  The compound represented by the general formula (P) can be synthesized by the method described in WO2003 / 060956, WO2004 / 080975 and the like. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.

In the organic electroluminescent element of the present invention, the compound represented by the general formula (P) is preferably contained in the organic layer between the light emitting layer and the cathode, but may be contained in a layer adjacent to the cathode. More preferred.
It is preferable that 70-100 mass% is contained with respect to the total mass of the organic layer to add, and, as for the compound represented by general formula (P), it is more preferable that 85-100 mass% is contained.

<Protective layer>
In the present invention, the entire organic electric field element may be protected by a protective layer.
Regarding the protective layer, the matters described in paragraph numbers [0169] to [0170] of JP-A-2008-270736 can be applied to the present invention. The material for the protective layer may be inorganic or organic.

<Sealing container>
The organic electroluminescent element of the present invention may be sealed entirely using a sealing container.
Regarding the sealing container, the matters described in paragraph No. [0171] of JP-A-2008-270736 can be applied to the present invention.

<Driving method>
The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Obtainable.
The driving method of the organic electroluminescent device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234658, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.

The external quantum efficiency of the organic electroluminescent element of the present invention is preferably 7% or more, more preferably 10% or more, and further preferably 12% or more. The value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency around 300 to 400 cd / m ² when the device is driven at 20 ° C. Can do.

  The internal quantum efficiency of the organic electroluminescence device of the present invention is preferably 30% or more, more preferably 50% or more, and further preferably 70% or more. The internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a normal organic EL element, the light extraction efficiency is about 20%. However, the substrate shape, electrode shape, organic layer thickness, inorganic layer thickness, organic layer refractive index, inorganic layer refractive index, etc. By devising it, it is possible to increase the light extraction efficiency to 20% or more.

<Emission wavelength>
There is no restriction | limiting in the light emission wavelength of the organic electroluminescent element of this invention. For example, among the three primary colors of light, it may be used for red light emission, green light emission, or blue light emission. Among them, the organic electroluminescent element of the present invention preferably has an emission wavelength of 500 to 700 nm from the viewpoint of the lowest excited triplet (T ₁ ) energy of the compound represented by the general formula (1).
Specifically, in the organic electroluminescent element of the present invention, when the compound represented by the general formula (1) is used as a host material of the light emitting layer, the emission wavelength is preferably 500 to 700 nm, and 520 to More preferably, it is 650 nm, and it is especially preferable that it is 520-550 nm.
On the other hand, in the organic electroluminescence device of the present invention, when the compound represented by the general formula (1) is used as a charge transport material for the hole blocking layer, the emission wavelength is preferably 400 to 700 nm, and 450 to 700 nm. More preferably, it is 650 nm, and it is especially preferable that it is 500-650 nm.

<Use of the organic electroluminescent device of the present invention>
The organic electroluminescent element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication. In particular, it is preferably used for a device that is driven in a region where light emission luminance is high, such as a light emitting device, a lighting device, and a display device.

[Light emitting device]
The light emitting device of the present invention includes the organic electroluminescent element of the present invention.
Next, the light emitting device of the present invention will be described with reference to FIG.
The light emitting device of the present invention uses the organic electroluminescent element.
FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention. The light emitting device 20 in FIG. 2 includes a transparent substrate (supporting substrate) 2, an organic electroluminescent element 10, a sealing container 16, and the like.

The organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2. A protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween. In addition, a part of each electrode 3 and 9, a partition, an insulating layer, etc. are abbreviate | omitted.
Here, as the adhesive layer 14, a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.

  The use of the light-emitting device of the present invention is not particularly limited, and for example, in addition to a lighting device, a display device such as a television, a personal computer, a mobile phone, and electronic paper can be used.

[Lighting device]
The illuminating device of this invention is characterized by including the organic electroluminescent element of this invention.
Next, the illumination device of the present invention will be described with reference to FIG.
FIG. 3 is a cross-sectional view schematically showing an example of the illumination device of the present invention. As shown in FIG. 3, the illumination device 40 of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
The light scattering member 30 is not particularly limited as long as it can scatter light. In FIG. 3, the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31. As the transparent substrate 31, for example, a glass substrate can be preferably cited. As the fine particles 32, transparent resin fine particles can be preferably exemplified. As the glass substrate and the transparent resin fine particles, known ones can be used. In such an illuminating device 40, when light emitted from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30, the incident light is scattered by the light scattering member 30, and the scattered light is emitted from the light emitting surface 30B. It is emitted as illumination light.

[Display device]
The display device of the present invention includes the organic electroluminescent element of the present invention. Examples of the display device of the present invention include a display device such as a television, a personal computer, a mobile phone, and electronic paper.

    The present invention will be described more specifically with reference to the following examples. The materials, amounts used, ratios, processing details, processing procedures, and the like shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below.

1. Synthesis Example The compound represented by the general formula (1) can be synthesized by combining the method described in JP-T 2010-535809 and other known reactions.
Synthesis Example 1 Synthesis of Compound 2

In an ice bath, 10.0 g (41.7 mmol) of 3-amino-5-bromobenzotrifluoride, 40 mL of pure water, and 20 mL of concentrated hydrochloric acid were stirred. A solution obtained by dissolving 3.74 g (54.2 mmol) of sodium nitrite in 15 mL of pure water was slowly added dropwise thereto. After stirring for 1 hour, a solution obtained by dissolving 13.8 g (83.4 mmol) of potassium iodide in 20 mL of pure water was slowly added dropwise, and the mixture was further added for 1 hour. After 1 hour, the ice bath was removed and the mixture was further stirred for 1 hour while naturally returning to room temperature. Toluene and pure water were added to the reaction solution for separation, and the organic layer was washed with an aqueous sodium thiosulfate solution. The organic layer was concentrated and purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate (9: 1)) to obtain 11.0 g of oily synthetic intermediate 1 (yield 75%). .
5.00 g (14.2 mmol) of synthetic intermediate 1, 3.24 g (14.2 mmol) of dibenzothiophene-4-boronic acid, 0.16 g (0.71 mmol) of palladium acetate, 0.75 g of triphenylphosphine (2. 84 mmol), 4.52 g (42.6 mmol) and dehydrated tetrahydrofuran were mixed and heated to reflux for 6.5 hours under a nitrogen atmosphere. After returning the reaction solution to room temperature, toluene was added for liquid separation, and the organic layer was purified by silica gel column chromatography (developing solvent: toluene). Then, 2.80 g of synthetic intermediate 2 was obtained by washing with methanol and hexane sequentially (yield 48%).
1.40 g (3.44 mmol) of synthetic intermediate 2 and 1.46 g (4.13 mmol) of 4,4,5,5-tetramethyl-2- (triphenylene-2-yl) -1,3,2-dioxaborane , 0.094 g (0.10 mmol) of tris (dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ), 0.17 g (0.41 mmol) of 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl (SPhos) ), 2.92 g (13.8 mmol) of potassium phosphate, 10 mL of toluene, and 10 mL of water were mixed and heated to reflux for 5 hours under a nitrogen atmosphere. The reaction solution was returned to room temperature, and the precipitated solid was filtered. The obtained solid was heated to reflux with THF and completely dissolved, 20 mL of toluene was added, and the THF was distilled off under heating to return to room temperature. The precipitated solid was filtered and washed with toluene to obtain 1.30 g of Compound 2 (yield 68%).
NMR data of Compound 2
¹ H NMR (400 MHz, in DMSO-d ₆ ); δ (ppm) = 9.27 (s, 1H), 9.15-9.12 (m, 1H), 8.98 (d, 1H), 8 91-8.84 (m, 3H), 8.66 (s, 1H), 8.53-8.44 (m, 3H), 8.25-8.22 (m, 1H), 8.15 (S, 1H), 8.09-8.07 (m, 1H), 7.88 (d, 1H), 7.77-7.72 (m, 5H), 7.60-7.54 (m , 2H) ppm.
Compounds 1 and 3 to 10 were also synthesized according to the synthesis method of Compound 2.

2. Element fabrication and evaluation All materials used for element fabrication were purified by sublimation, and it was confirmed by high performance liquid chromatography (Tosoh TSKgel ODS-100Z) that the purity (absorption intensity area ratio at 254 nm) was 99.9% or higher. . Comparative compound 1 and comparative compound 2 are compounds 2S and 2O described in JP-T 2010-535809, respectively, and comparative compound 3 is compound 3-45 described in International Publication WO2009 / 074087.

Example 1
A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, ultrasonically cleaned in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic compound layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
First layer: HAT-CN: film thickness 10 nm
Second layer: NPD: film thickness 30 nm
Third layer: Host material described in Table 1 and GD-1 (mass ratio 90:10): film thickness 30 nm
Fourth layer: HBL material described in Table 1: film thickness 5 nm
Fifth layer: Alq: film thickness 45 nm
On top of this, 0.1 nm of lithium fluoride and 100 nm of metallic aluminum were vapor-deposited in this order to form a cathode.
The obtained laminate is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.) are used. Then, elements 1-1 to 1-7 and comparative elements 1-1 to 1-5 were obtained. The light emitting portion is a 2 mm × 2 mm square. Table 1 shows the results of evaluating these elements from the viewpoints of efficiency, drive voltage, durability, and efficiency after high-temperature storage by the following methods.

(A) Efficiency after high-temperature storage Each element is stored in a thermostat at 105 ° C. for 100 hours, and then a direct voltage is applied to each element to emit light using a source measure unit 2400 made by Toyo Technica. Measurement was performed using a luminance meter BM-8. Based on these, the external quantum efficiency (η) with a luminance of around 1000 cd / m ² was calculated by the luminance conversion method. In Table 1, the value of the comparison element 1-1, in Table 2, the value of the comparison element 2-1, in Table 3, the value of the comparison element 3-1, and in Table 4, the value of the comparison element 4-1. In Table 5, the value of the comparison element 5-1 was shown, and in Table 6, the value of the comparison element 6-1 was 1.0. The higher the number, the better the efficiency.

(B) after 100 hours storage the driving durability each element after high-temperature storage in a thermostat at 105 ° C., continue to emit light by applying a DC voltage so that the luminance becomes 5000 cd / m ^2, the luminance is 4000 cd / m ^The time taken to reach ² was used as an index of durability. In Table 1, the value of the comparison element 1-1, in Table 2, the value of the comparison element 2-1, in Table 3, the value of the comparison element 3-1, and in Table 4, the value of the comparison element 4-1. In Table 5, the value of the comparison element 5-1 was shown, and in Table 6, the value of the comparison element 6-1 was 1.0. The larger the number, the better the durability.

(C) Dark spots When 10 elements were manufactured under the same conditions and the light emitting surface was observed while emitting each element with a luminance of 4000 cd / m ² under a microscope, the presence of dark spots was observed in 6 or more elements. When confirmed, it was indicated as XX, when existence of a dark spot was confirmed with 2 to 5 elements, and when it was confirmed that the existence of a dark spot was 1 or less, it was indicated as ◯.

上記表１より、発光層のホスト化合物として化合物１、４、７〜９の一般式（１）で表される化合物を用いた各実施例の有機電界発光素子は、いずれも高温保管後の効率、駆動耐久性が良好であり、ダークスポットも見られないことがわかった。
一方、比較例１、２の有機電界発光素子は、発光層のホスト化合物として比較化合物１、２を用いたものであり、高温保管後の効率、駆動耐久性が悪く、ダークスポットの発生が顕著であった。また、比較化合物３を用いた比較素子１−３では、発光材料ＧＤ−１の発光が確認できなかった。
なお、実施例１で作製した有機電界発光素子の発光波長は５２２〜５２８ｎｍであった。

From Table 1 above, the organic electroluminescent elements of the respective examples using the compounds represented by the general formula (1) of compounds 1, 4, and 7 to 9 as the host compound of the light emitting layer are all efficient after high temperature storage. It was found that the driving durability was good and no dark spots were observed.
On the other hand, the organic electroluminescent elements of Comparative Examples 1 and 2 are those using Comparative Compounds 1 and 2 as the host compound of the light emitting layer. The efficiency and driving durability after storage at high temperatures are poor, and the occurrence of dark spots is remarkable. Met. Moreover, in the comparative element 1-3 using the comparative compound 3, light emission of the light emitting material GD-1 could not be confirmed.
Note that the emission wavelength of the organic electroluminescent element produced in Example 1 was 522 to 528 nm.

(Example 2)
Table 2 shows the results obtained by fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm
Second layer: NPD: film thickness 5 nm
Third layer: HT-1: film thickness 3 nm
Fourth layer: H-1 and GD-2 (mass ratio 85:15): film thickness 30 nm
Fifth layer: HBL material described in Table 2: film thickness 10 nm
Sixth layer: ET-2: film thickness 20 nm

From the above Table 2, the organic electroluminescent elements of the respective examples using the compounds represented by the general formula (1) of the compounds 2, 5 and 6 as the material of the hole blocking layer are all the efficiency after high temperature storage, It was found that the driving durability was good and no dark spots were seen.
On the other hand, the organic electroluminescent elements of Comparative Examples 1 and 2 are those using Comparative Compounds 1 and 2 as the material of the hole blocking layer, and the efficiency after high-temperature storage and driving durability are poor, and dark spots are generated. It was remarkable.
In addition, the light emission wavelength of the organic electroluminescent element produced in Example 2 was 503 to 507 nm.

(Example 3)
Table 3 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
First layer: CuPc: film thickness 10 nm
Second layer: NPD: film thickness 30 nm
Third layer: Host material described in Table 3 and RD-1 (mass ratio 95: 5): film thickness 30 nm
Fourth layer: ET-2: film thickness 5 nm
Fifth layer: ET-3: Film thickness 50 nm

From Table 3 above, the organic electroluminescent devices of the respective examples using the compounds represented by the general formula (1) of compounds 3 to 5 and 10 as the host compound of the light emitting layer are all efficient and driven after high temperature storage. It was found that the durability was good and no dark spots were seen.
On the other hand, the organic electroluminescent elements of Comparative Examples 1 and 2 are those using Comparative Compounds 1 and 2 as the host compound of the light emitting layer. The efficiency and driving durability after storage at high temperatures are poor, and the occurrence of dark spots is remarkable. Met.
Note that the emission wavelength of the organic electroluminescent element produced in Example 3 was 618 to 622 nm.

Example 4
Table 4 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
First layer: TCTA: film thickness 35 nm
Second layer: HT-2: film thickness 5 nm
Third layer: BAlq and RD-2 (mass ratio 90:10): film thickness 30 nm
Fourth layer: HBL material described in Table 4: film thickness 5 nm
Fifth layer: ET-4: Film thickness 45 nm

From Table 4 above, the organic electroluminescent elements of the examples using the compounds represented by the general formula (1) of the compounds 3, 7 and 8 as the material of the hole blocking layer are all the efficiency after high temperature storage, It was found that the driving durability was good and no dark spots were seen.
On the other hand, the organic electroluminescent elements of Comparative Examples 1 and 2 were those using Comparative Compounds 1 and 2 as the material of the hole blocking layer, and the efficiency after high-temperature storage and the driving durability were poor.
Note that the emission wavelength of the organic electroluminescent element produced in Example 4 was 625 to 629 nm.

(Example 5)
Table 5 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
First layer: HAT-CN: film thickness 10 nm
Second layer: NPD: film thickness 115 nm
Third layer: HT-3: film thickness 5 nm
Fourth layer: H-2 and Firepic (mass ratio 90:10): film thickness 30 nm
Fifth layer: HBL material described in Table 5: film thickness 5 nm
Sixth layer: ET-5: film thickness 25 nm

From the above Table 5, the organic electroluminescent elements of the respective examples using the compounds represented by the general formula (1) of the compounds 1, 2 and 6 as the material of the hole blocking layer are all the efficiency after high temperature storage, It was found that the driving durability was good and no dark spots were seen. On the other hand, the organic electroluminescent elements of Comparative Examples 1 and 2 are those using Comparative Compounds 1 and 2 as the material of the hole blocking layer, and the efficiency after high-temperature storage and driving durability are poor, and dark spots are generated. Admitted.
Note that the emission wavelength of the organic electroluminescent element produced in Example 5 was 472 to 476 nm.

(Example 6)
Table 6 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 120 nm
Second layer: NPD: film thickness 7 nm
Third layer: HT-3: film thickness 3 nm
Fourth layer: H-3 and BD-1 (mass ratio 85:15): film thickness 30 nm
Fifth layer: HBL material described in Table 6: film thickness 5 nm
Sixth layer: BAlq: film thickness 25 nm

From Table 6 above, the organic electroluminescent elements of the Examples using the compounds represented by the general formula (1) of the compounds 3, 5 and 7 as the material of the hole blocking layer are all the efficiency after high-temperature storage, It was found that the driving durability was good and no dark spots were seen.
On the other hand, the organic electroluminescent elements of Comparative Examples 1 and 2 are those using Comparative Compounds 1 and 2 as the material of the hole blocking layer, and the efficiency after high-temperature storage and driving durability are poor, and dark spots are generated. Admitted.
In addition, the light emission wavelength of the organic electroluminescent element produced in Example 6 was 455 to 460 nm.

DESCRIPTION OF SYMBOLS 2 ... Substrate 3 ... Anode 4 ... Hole injection layer 5 ... Hole transport layer 6 ... Light emitting layer 7 ... Hole block layer 8 ... Electron transport layer 9 ... -Cathode 10 ... Organic electroluminescent element 11 ... Organic layer 12 ... Protective layer 14 ... Adhesive layer 16 ... Sealing container 20 ... Light emitting device 30 ... Light scattering member 31 ..Transparent substrate 30A ... light incident surface 30B ... light exit surface 32 ... fine particles 40 ... illumination device

Claims (16)

A charge transport material comprising a compound represented by the following general formula (1).

(In the general formula (1), X ¹⁰¹ represents a sulfur atom or an oxygen atom. R ¹⁰¹ and R ¹⁰² each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and these groups in .n101 which may be substituted represents an integer of 0 to 11, n102 represents an integer of 0 to 7, a plurality of R ¹⁰¹ and R ¹⁰² are optionally be the same or different .L ¹⁰¹ represents a single bond or Represents a divalent linking group, wherein any of R ¹⁰¹ , L ¹⁰¹ and R ¹⁰² represents a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a cycloalkylene group, a silyl group, an alkylsilyl group, an arylsilyl group or silicon Including atom linking group.) The charge transport material according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (2).

(In the general formula (2), X ¹¹¹ represents a sulfur atom or an oxygen atom. R ¹¹¹ , R ¹¹² and R ¹¹³ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, N111 represents an integer of 0 to 11, n112 represents an integer of 0 to 7, n113 represents an integer of 0 to 4, and a plurality of R ¹¹¹ , R ¹¹² and R may be substituted with these groups. ¹¹³ may be the same or different, A ^{A1 to} A ^A5 each independently represent CH (the hydrogen atom of CH may be substituted with R ¹¹³ ) or a nitrogen atom, and m111 represents an integer of 0 to 6; represented. However, any of R ^111, R ¹¹² and R ^113, includes a fluorine atom, fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group or an aryl silyl group, n111, n112 Oyo n113 is not equal to 0 at the same time.)   The charge transport material according to claim 2, wherein m111 in the general formula (2) is 1 to 5. The charge transport material according to any one of claims 1 to 3, wherein the compound represented by the general formula (1) is represented by the following general formula (3).

(In the general formula (3), X ¹²¹ represents a sulfur atom or an oxygen atom. R ¹²¹ , R ¹²² and R ¹²³ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group; N121 represents an integer of 0 to 11, n122 represents an integer of 0 to 7, n123 represents an integer of 0 to 4, and a plurality of R ¹²¹ , R ¹²² and R may be substituted with these groups. ¹²³ may be the same or different, and m121 represents an integer of 0 to 6. However, any one of R ¹²¹ , R ¹²² , and R ¹²³ represents a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, or an alkyl group. (Including silyl group or arylsilyl group, n121, n122 and n123 are not 0 at the same time.)   The charge transport material according to claim 1, wherein n101 in the general formula (1) is 0.   Charge transport material as described in any one of Claims 1-5 whose n102 in the said General formula (1) is an integer of 0-2.   The compound represented by the general formula (1) is composed of only carbon atoms and hydrogen atoms, excluding oxygen atoms and sulfur atoms in the dibenzothiophene skeleton and dibenzofuran skeleton. The charge transport material according to one item.   The charge transport material according to any one of claims 1 to 7, wherein the compound represented by the general formula (1) includes a cycloalkyl group.   The molecular weight of the compound represented by General formula (1) is 1200 or less, The charge transport material as described in any one of Claims 1-8 characterized by the above-mentioned. A substrate,
A pair of electrodes disposed on the substrate, including an anode and a cathode;
An organic layer disposed between the electrodes,
The said organic layer contains a phosphorescence-emitting material and the electric charge transport material as described in any one of Claims 1-9, The organic electroluminescent element characterized by the above-mentioned. The organic electroluminescent element according to claim 10, wherein the phosphorescent material is represented by the following general formula (E-1).

(In General Formula (E-1), Z ¹ and Z ² each independently represents a carbon atom or a nitrogen atom. A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle together with Z ¹ and the nitrogen atom. B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom, (XY) represents a monoanionic bidentate ligand, and n _E1 is an integer of 1 to 3. Represents.) The organic electroluminescent element according to claim 11, wherein the phosphorescent material represented by the general formula (E-1) is represented by the following general formula (E-2).

(In the formula (E-2), the A ^E1 to A ^E8 each independently a nitrogen atom or,, .R ^E representing a carbon atom substituted with R ^E represents a hydrogen atom or a substituent. (X- Y) represents a monoanionic bidentate ligand, and n _E2 represents an integer of 1 to 3.)   The organic electroluminescent element according to claim 11 or 12, wherein the phosphorescent material represented by the general formula (E-1) has a maximum emission wavelength of 500 nm to 700 nm. The organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
The organic light-emitting device according to claim 10, wherein the light-emitting layer contains a compound represented by the general formula (1). The organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
The other organic layer includes a hole blocking layer disposed between the light emitting layer and the cathode, and the hole blocking layer contains the compound represented by the general formula (1). The organic electroluminescent element according to any one of claims 10 to 14.   A light emitting device, a display device, or a lighting device using the organic electroluminescent element according to any one of claims 10 to 15.

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